200636-42-6

Basic information

• Product Name: (Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol
• Synonyms: (Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol
• CAS NO: 200636-42-6
• Molecular Weight: 587.076
• Mol File: 200636-42-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 545.2±50.0 °C(Predicted)
• Density: 0.94±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol(200636-42-6)
• EPA Substance Registry System: (Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol(200636-42-6)

Safety Data

• Hazardous Substances Data: 200636-42-6(Hazardous Substances Data)

Usage

General Description

(Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol, also known as TBDMS-PROTECTED (3S,4S,5S)-3,4,5-ISODEDOXABICYCLO[4.3.0]NONAN-2-ONE, is a chemical compound with a complex structure. It contains a cyclohexylidene ring and several tert-butyldimethylsilyloxy groups, which are protective groups often used in organic synthesis. The compound also has an ethanol functional group. It is commonly used as an intermediate or precursor in the synthesis of other organic compounds, and its specific structure and properties make it useful in the development of various pharmaceuticals and agrochemicals. The tert-butyldimethylsilyloxy groups serve to protect reactive sites in the molecule during reactions, and can be removed under specific conditions to reveal the underlying functionality.

Upstream product

• 200636-33-5 2,2-Dimethyl-propionic acid (2R,3R)-2-[3-(2,2-dimethyl-propionyloxy)-propoxy]-3-hydroxy-7-(4-methoxy-benzyloxy)-1-vinyl-hept-5-ynyl ester 
• 933779-90-9 (5R,6R,7RS)-5,7-bis(tert-butyldimethylsilyloxy)-6-(3-tert-butyldimethylsilyloxypropoxy)non-8-en-2-yn-1-ol 
• 337970-23-7 (2R,3S,4RS)-1,2-O-isopropylidene-4-pivaloyloxy-3-(3-pivaloyloxypropoxy)-5-hexene-1,2-diol 
• 200636-30-2 (2R,3S,4RS)-1,2-epoxy-4-pivaloyloxy-3-(3-pivaloyloxypropoxy)-5-hexene 
• 337970-24-8 (2R,3S,4RS)-4-pivaloyloxy-3-(3-pivaloyloxypropoxy)-5-hexene-1,2-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 200636-38-0 (Z,5R,6R,7RS)-5,7-bis(tert-butyldimethylsilyloxy)-6-(3-tert-butyldimethylsilyloxypropoxy)-3-iodonona-2,8-dien-1-ol 
• 1101867-34-8 methyl (3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarboxylate 
• 897014-96-9 (-)-methyl 4-epi-shikimate 
• 200636-28-8 2,2-Dimethyl-propionic acid 3-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-but-3-enyloxy]-propyl ester 

Downstream Products

• 200636-54-0 [3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide 
• 104121-92-8 Eldecalcitol 
• 200636-50-6 [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane 

Relevant articles and documents

A (Z)- 2 - ((3R, 4R, 5R) - 3, 5 - double-hydroxy - 4 - (3 - hydroxy - propoxy) - 2 - methylene-cyclohexyl) ethanol derivatives of the preparation method of the A

The invention discloses a new preparation method of a derivative A of a key Ayr calciferol intermediate (Z)-2-((3R,4R,5R)-3,5-dihydroxy-4-(3-hydroxy-propoxy)-2-methylene cyclohexyl) ethanol. The method comprises the following steps: performing 3,5-hydroxy protection on a compound 1 serving as a starting material, then reacting the protected compound 1 with R2O(CH2)3X to protect 4-hydroxy, oxidizing with a permanganate to obtain 1,2-hydroxy, performing further oxidation and wittig reaction to obtain 2-methylene, reducing, oxidizing, reacting the oxidized product with trimethyl silicon-based ethyl acetate, and performing DiBAL-H reduction to obtain a compound A. Compared with the prior art, illumination reaction is not used in the new route, so that the operation is simple and amplification is facilitated; and the used raw materials are cheap and readily available natural products, and all chiral centers are introduced from the raw materials, so the cost is low and the quality of the compound A is easy to control.

Convergent synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

A convergent and versatile synthesis of the potent vitamin D analog, 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 [1] (ED-71) is described.