(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate

Base Information

• Chemical Name: (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate
• CAS No.: 1376709-28-2
• Molecular Formula: C₁₇H₂₉ClO₃Si
• Molecular Weight: 344.954
• Mol file: 1376709-28-2.mol

Synonyms:(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate

Chemical Property of (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate

There total 3 articles about (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate 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: 96.0%

(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate (1376709-27-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate (1376709-28-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/ja303529z

Reference yield:

(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (90129-47-8) → (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate (1376709-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: calcium hypochlorite / dichloromethane; water / 2 h / Cooling with ice

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 3 h / 0 - 20 °C / Inert atmosphere

3: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.17 h / -78 - 20 °C / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; calcium hypochlorite; cerium(III) chloride heptahydrate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: Mitsunobu reaction / 3: Luche reduction;

DOI:10.1021/ja303529z

Reference yield:

(1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate (1376709-10-2) → (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate (1376709-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.17 h / -78 - 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; N,N-dimethyl-formamide; 1: Luche reduction;

DOI:10.1021/ja303529z

upstream raw materials:

(1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate

(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate

tert-butyldimethylsilyl chloride

(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Downstream raw materials:

C₃₃H₄₄O₅

(4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-iodoprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate