Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate
• CAS No.: 101906-39-2
• Molecular Formula: C₂₀H₄₀O₅Si₂
• Molecular Weight: 416.706
• Mol file: 101906-39-2.mol

Synonyms:Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

Chemical Property of Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

There total 4 articles about Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(3R,5R)-3,5-bis-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(trimethylsilyl)oxy]cyclohexanecarboxylic acid methyl ester → Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2)

Guidance literature:

(3R,5R)-3,5-bis-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(trimethylsilyl)oxy]cyclohexanecarboxylic acid methyl ester; With pyridine; sulfuryl dichloride; In dichloromethane; at -78 ℃; for 5h; Inert atmosphere;

In methanol; at -78 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01295

Reference yield: 95.0%

methyl shikimate (40983-58-2) + tert-butyldimethylsilyl chloride (18162-48-6) → Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 12h;

DOI:10.1002/hlca.200790138

Reference yield:

shikimic acid (138-59-0) → Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / (+) cation resin / 15 h / Heating

2: 95 percent / 1H-imidazole; DMAP / dimethylformamide / 12 h / 0 - 25 °C

With 1H-imidazole; dmap; In N,N-dimethyl-formamide;

DOI:10.1002/hlca.200790138

upstream raw materials:

methyl shikimate

tert-butyldimethylsilyl chloride

shikimic acid

Downstream raw materials:

methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methylsulfonylshikimate

(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

1α,25-dihydroxy-2-methylene-vitamin D₃

(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne