(2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

Base Information

Chemical Name:(2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol
CAS No.:330150-91-9
Molecular Formula:C₂₅H₃₆O₃Si
Molecular Weight:412.645
Hs Code.:

Synonyms:(2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

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Chemical Property of (2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

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Technology Process of (2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

There total 5 articles about (2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol 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: 78.0%

: 590-18-1
(Z)-2-Butene

: 330150-89-5
(S)-4-((tert-butyldiphenylsilyl)oxy)-3-methoxybutanal

: 330150-91-9
(2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; (+)-B-methoxydiisocamphenylborane; at -78 ℃; for 4h;
DOI:10.1002/1099-0690(200101)2001:1<39::AID-EJOC39>3.0.CO;2-9

Reference yield: 72.0%

: 99438-30-9
(Z)-(+)-crotyldiisopinocampheyl borane

: 330150-89-5
(S)-4-((tert-butyldiphenylsilyl)oxy)-3-methoxybutanal

: 330150-91-9
(2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

Guidance literature:: (Z)-(+)-crotyldiisopinocampheyl borane; (S)-4-((tert-butyldiphenylsilyl)oxy)-3-methoxybutanal; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 4h;

With sodium hydroxide; dihydrogen peroxide;
DOI:10.1002/1099-0690(200203)2002:5<785::AID-EJOC785>3.0.CO;2-N

Reference yield:

: 124655-05-6
(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

: 330150-91-9
(2S,4S,5S)-1-O-(tert-butyldiphenylsilyl)-5-methyl-2-O-methyl-6-hepten-1,2,4-triol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 14 h / 25 °C

2.1: 85 percent / DIBAL-H / CH₂Cl₂ / 2 h / -80 °C

3.1: BF₃*Et₂O / tetrahydrofuran / 4 h / -78 °C

3.2: 72 percent / aq. NaOH; H₂O₂

With 2,6-di-tert-butyl-pyridine; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1099-0690(200203)2002:5<785::AID-EJOC785>3.0.CO;2-N