(2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

Base Information

Chemical Name:(2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol
CAS No.:863488-33-9
Molecular Formula:C₃₅H₄₈O₄Si
Molecular Weight:560.849
Hs Code.:

Synonyms:(2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

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Chemical Property of (2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

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Technology Process of (2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

There total 4 articles about (2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol 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: 93.0%

: 863488-32-8
(2S,3R,4S,5R,6S)-1-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-heptane-3,5-diol

: 77-76-9
2,2-dimethoxy-propane

: 863488-33-9
(2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

Guidance literature:: With PPTC; In dichloromethane; at 20 ℃;
DOI:10.1021/jo050792l

Reference yield:

: 863488-30-6
(2S,4R,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-2,4-dimethyl-3-heptanone

: 863488-33-9
(2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₂BOMe / tetrahydrofuran / 0.33 h / -78 °C

1.2: NaBH₄ / tetrahydrofuran / 3 h / -78 °C

1.3: 50 mg / NaOAc; H₂O₂ / H₂O; methanol / 1 h / 20 °C

2.1: 93 percent / PPTC / CH₂Cl₂ / 20 °C

With diethyl methoxy borane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo050792l

Reference yield:

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 863488-33-9
(2S,3R,4S,5R,6S)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-3,5-O-isopropylidene-2,4-dimethyl-3,5-heptanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: (i-PrO)4Ti; TiCl₄; i-Pt₂NEt / CH₂Cl₂ / 2 h / -78 °C

1.2: CH₂Cl₂ / 1 h / -78 °C

2.1: Et₂BOMe / tetrahydrofuran / 0.33 h / -78 °C

2.2: NaBH₄ / tetrahydrofuran / 3 h / -78 °C

2.3: 50 mg / NaOAc; H₂O₂ / H₂O; methanol / 1 h / 20 °C

3.1: 93 percent / PPTC / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; diethyl methoxy borane; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: aldol reaction;
DOI:10.1021/jo050792l