Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
Bis-TBDMS-trans-calcipotriol (CAS: 112849-27-1), also known as Bis-O-(tert-butyldimethylsilyl)-trans-calcipotriol, is a key synthetic intermediate for calcipotriol (calcipotriene)—a potent synthetic analog of vitamin D? used in treating psoriasis. It is a protected form of trans-calcipotriol, with two secondary hydroxyl groups on the A-ring masked as tert-butyldimethylsilyl (TBDMS) ethers to prevent unwanted side reactions during synthesis. It appears as an off-white powder or clear oil, chemically stable but biologically inert, widely used in medicinal chemistry and pharmaceutical R&D.
Uses
Pharmaceutical R&D: A critical intermediate in the synthesis of calcipotriol, a cornerstone therapy for psoriasis that modulates gene expression by binding to the vitamin D receptor (VDR). The TBDMS protecting groups enable selective synthetic modifications, ensuring the formation of the active drug molecule after deprotection.
Chemical Research: Used as a model compound for studying protecting group strategies in steroid and vitamin D derivative synthesis. It also serves as an analytical reference standard and impurity control reagent in pharmaceutical quality control processes for calcipotriol-based drugs.
Molecular Formula & Structure
- Molecular Formula: C??H??O?Si?
- Molecular Weight: 641.13 g/mol
- IUPAC Name: Bis-O-(tert-butyldimethylsilyl)-trans-calcipotriol
- Synonyms: Trans-Calcipotriol-bis-TBDMS-ether;
- InChIKey: DIMYHZDULFSWLS-FXKXXENDNA-N
- SMILES Code: (C@)12(C)CCC/C(=C\C=C3/C(C@@H)(O(Si)(C)(C)C(C)(C)C)C(C@H)(O(Si)(C)(C)C(C)(C)C)C/3=C)/(C@)1((H))CC(C@@H)2(C@H)(C)/C=C/(C@@H)(O)C1CC1 |&1:0,10,20,31,35,36,40,r|
- Chemical Structure: A steroid-derived structure with a vitamin D? backbone, featuring two TBDMS (tert-butyldimethylsilyl) protecting groups attached to the secondary hydroxyl groups of the A-ring. This protected structure ensures chemical stability during the synthesis of the active drug calcipotriol.
Physical & Chemical Properties
- Appearance: Off-white powder or clear oil, no obvious odor, no visible impurities.
- Density: 0.98±0.1 g/cm3 (25 °C, predicted); Refractive Index: 1.515
- Solubility: Insoluble in water; soluble in organic solvents such as DMSO, dichloromethane, and ethyl acetate; compatible with common organic reaction solvents.
- Boiling Point: 628.2±55.0 °C (predicted); Flash Point: 333.7 °C
- Stability: Chemically stable under normal temperature and dry conditions; incompatible with strong oxidants and strong acids/bases; the TBDMS groups are susceptible to deprotection under acidic conditions; avoid light, moisture and high temperature.
- Toxicity: Low toxicity; mild irritation to skin and eyes upon direct contact; non-toxic by oral ingestion; handle with standard laboratory protective measures.
- pKa: 14.29±0.20 (predicted); LogP: 11.15; PSA: 38.69 ?2
Synthesis & Storage
- Synthesis: Typically prepared by the TBDMS protection reaction of trans-calcipotriol, using tert-butyldimethylsilyl chloride (TBDMSCl) as the protecting reagent in the presence of a base (such as imidazole), followed by purification via column chromatography or recrystallization to obtain high-purity products.
- Storage: Sealed in amber vials under inert atmosphere; stored in a -20 °C freezer for long-term storage, or 2–8 °C for short-term storage; avoid light, moisture, high temperature and strong oxidants; shelf life is 1–2 years under proper storage conditions.
- Safety: Operate in a well-ventilated fume hood; wear professional protective gear (gloves, goggles, lab coat) to avoid direct contact with skin and eyes; wash thoroughly with soap and water after handling; dispose of waste in accordance with pharmaceutical chemical waste regulations.
...
Product
