(-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate

Base Information

• Chemical Name: (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate
• CAS No.: 1309661-67-3
• Molecular Formula: C₁₄H₂₄O₄Si
• Molecular Weight: 284.428
• Mol file: 1309661-67-3.mol

Synonyms:(-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate

Chemical Property of (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate

There total 3 articles about (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate 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: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + (-)-(1S,6R)-methyl 1,6-dihydroxycyclohexa-2,4-dienecarboxylate (172877-72-4) → (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate (1309661-67-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 12h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol201057r

Reference yield:

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9) → (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate (1309661-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

2: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 20 h / 25 °C / Inert atmosphere; Schlenk technique

With 1H-imidazole; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.7b00194

Reference yield:

sodium benzoate (532-32-1) → (-)-(1S,6R)-methyl-6-((tert-butyldimethylsilyl)oxy)-1-hydroxycyclohexa-2,4-dienecarboxylate (1309661-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: D-fructose / water / Microbiological reaction

1.2: 0 - 5 °C / pH Ca_. 5

2.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

3.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 20 h / 25 °C / Inert atmosphere; Schlenk technique

With 1H-imidazole; D-fructose; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.7b00194

upstream raw materials:

t-butyldimethylsiyl triflate

(-)-(1S,6R)-methyl 1,6-dihydroxycyclohexa-2,4-dienecarboxylate

sodium benzoate

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid