(3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

Base Information

Chemical Name:(3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol
CAS No.:103563-52-6
Molecular Formula:C₁₉H₃₂O₃Si
Molecular Weight:336.547
Hs Code.:

Synonyms:(3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

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Chemical Property of (3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

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Technology Process of (3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

There total 12 articles about (3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-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: 95.0%

: 103563-51-5
(R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-one

: 103563-52-6
(3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)89230-8

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 103563-52-6
(3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: NaH

2: EtMgBr

3: DIBAL, Br₂

4: 92 percent / n-BuLi / tetrahydrofuran; diethyl ether; hexane / 0.5 h

5: Et₃N / CH₂Cl₂ / 0.33 h / -45 °C

6: DIBAL, Et₃Al / CH₂Cl₂ / 2 h / -78 - -20 °C

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

8: diethyl ether / -78 °C

With n-butyllithium; oxalyl dichloride; ethylmagnesium bromide; bromine; triethylaluminum; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00277a028

Reference yield:

: 96011-46-0
3-(benzyloxymethoxy)prop-1-yne

: 103563-52-6
(3R,4R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: EtMgBr

2: DIBAL, Br₂

3: 92 percent / n-BuLi / tetrahydrofuran; diethyl ether; hexane / 0.5 h

4: Et₃N / CH₂Cl₂ / 0.33 h / -45 °C

5: DIBAL, Et₃Al / CH₂Cl₂ / 2 h / -78 - -20 °C

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

7: diethyl ether / -78 °C

With n-butyllithium; oxalyl dichloride; ethylmagnesium bromide; bromine; triethylaluminum; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00277a028