(E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

Base Information

Chemical Name:(E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate
CAS No.:1432620-37-5
Molecular Formula:C₂₁H₃₆O₃Si
Molecular Weight:364.601
Hs Code.:

Synonyms:(E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

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Chemical Property of (E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

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Technology Process of (E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

There total 3 articles about (E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate 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%

: 1432620-35-3
(E)-(1R,4R,6R)-4-hydroxy-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 1432620-37-5
(E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 0.25h; diastereoselective reaction;
DOI:10.1039/c3ob40120k

Reference yield:

: 1432620-33-1
(E)-(1R,6R)-3-methyl-4-oxo-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

: 1432620-37-5
(E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 2,6-dimethylpyridine / dichloromethane / 0.25 h

With 2,6-dimethylpyridine; cerium(III) chloride heptahydrate; In methanol; dichloromethane; 1: |Mitsunobu Displacement / 2: |Mitsunobu Displacement;
DOI:10.1039/c3ob40120k

Reference yield:

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

: 1432620-37-5
(E)-(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl pent-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 2,6-dimethylpyridine / dichloromethane / 0.25 h

With 2,6-dimethylpyridine; cerium(III) chloride heptahydrate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: |Mitsunobu Displacement / 2: |Mitsunobu Displacement / 3: |Mitsunobu Displacement;
DOI:10.1039/c3ob40120k