(1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester

Base Information

• Chemical Name: (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester
• CAS No.: 173914-19-7
• Molecular Formula: C₁₈H₃₀O₆Si
• Molecular Weight: 370.518
• Mol file: 173914-19-7.mol

Synonyms:(1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester

Chemical Property of (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester

There total 3 articles about (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester 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: 74.0%

Lithium allyl alcoholate (52203-12-0) + (1S,4S,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-4-carboxylic acid methyl ester (162273-01-0) → (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester (173914-19-7)

Guidance literature:

DOI:10.1016/S0040-4039(00)78338-9

Reference yield:

methyl 2-oxo-2H-pyrane-3-carboxylate (25991-27-9) → (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester (173914-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / (R)-(+)-1,1'-bi-2-naphthol titanium dichloride diisopropoxide complex / toluene / 24 h / -30 °C

2: 74 percent

With (R)-(+)-1,1'-bi-2-naphthol titanium dichloride diisopropoxide; In toluene;

DOI:10.1016/S0040-4039(00)78338-9

Reference yield:

tert-butyldimethylsilyl vinyl ether (66031-93-4) → (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester (173914-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / (R)-(+)-1,1'-bi-2-naphthol titanium dichloride diisopropoxide complex / toluene / 24 h / -30 °C

2: 74 percent

With (R)-(+)-1,1'-bi-2-naphthol titanium dichloride diisopropoxide; In toluene;

DOI:10.1016/S0040-4039(00)78338-9

upstream raw materials:

Lithium allyl alcoholate

(1S,4S,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-4-carboxylic acid methyl ester

methyl 2-oxo-2H-pyrane-3-carboxylate

tert-butyldimethylsilyl vinyl ether

Downstream raw materials:

(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

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