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

Base Information

Chemical Name:(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate
CAS No.:1376709-27-1
Molecular Formula:C₁₁H₁₅ClO₃
Molecular Weight:230.691
Hs Code.:

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

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

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

There total 3 articles about (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-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: 92.0%

: 1376709-10-2
(1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate

: 1376709-27-1
(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at -78 - 20 ℃; for 0.166667h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ja303529z

Reference yield:

: 90129-47-8
(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

: 1376709-27-1
(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate

Guidance literature:: Multi-step reaction with 3 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

With sodium tetrahydroborate; calcium hypochlorite; cerium(III) chloride heptahydrate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 2: Mitsunobu reaction / 3: Luche reduction;
DOI:10.1021/ja303529z

Reference yield:

: 1376709-08-8
(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

: 1376709-27-1
(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate

Guidance literature:: Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 1: Mitsunobu reaction / 2: Luche reduction;
DOI:10.1021/ja303529z