(3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

Base Information

Chemical Name:(3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol
CAS No.:1536053-88-9
Molecular Formula:C₂₃H₃₂O₃Si
Molecular Weight:384.591
Hs Code.:

Synonyms:(3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

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Chemical Property of (3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

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Technology Process of (3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

There total 1 articles about (3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol 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:

: 103223-44-5
(buta-1,3-dien-2-yl)dimethyl(phenyl)silane

: 135362-69-5
3-(4-methoxybenzyl)oxypropan-1-ol

: 1536053-88-9
(3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

: C₂₃H₃₂O₃Si

Guidance literature:: With (R)-(+)-(4,4'-bi-1,3-benzodioxole)-5,5'-diylbis(di(3,5-dimethylphenyl)phosphine); (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); sodium sulfate; In toluene; at 95 ℃; for 48h; Overall yield = 75 %; Overall yield = 4.4 g; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol403566w

Reference yield: 87.0%

: 1536053-88-9
(3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

: 1536053-91-4
((R)-3-((2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-1-en-2-yl)dimethyl(phenyl)silane

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at -15 ℃; for 10h; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol403566w

Reference yield:

: 1536053-88-9
(3S,4R)-5-(dimethyl(phenyl)silyl)-1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol

: 1536054-15-5
(2R,5R)-6-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)-5-((tert-butyldimethylsilyl)oxy)-2-((2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)hexan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 10 h / -15 °C / Molecular sieve; Inert atmosphere

2.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 0 °C / Inert atmosphere

3.1: sodium methylate / methanol / 3 h / 80 °C / Inert atmosphere

4.1: tert.-butyl lithium / diethyl ether / 2 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 - -40 °C / Inert atmosphere

4.3: 2 h / -78 - -10 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: ozone; Sudan III / dichloromethane; methanol / 0.13 h / -78 °C

6.2: 0.5 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; pyridinium hydrobromide perbromide; tert.-butyl lithium; sodium methylate; ozone; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Sudan III; In methanol; diethyl ether; dichloromethane;
DOI:10.1021/ol403566w