(E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester
CAS No.:142138-46-3
Molecular Formula:C₂₉H₅₂O₆Si₂
Molecular Weight:552.899
Hs Code.:

Synonyms:(E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

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Chemical Property of (E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

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Technology Process of (E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

There total 10 articles about (E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester 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: 79.0%

: 142138-40-7
(E)-(4R,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-oct-6-enoic acid ethyl ester

: 142138-46-3
(E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; at -78 - 40 ℃; for 20h;
DOI:10.1021/jo00075a024

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 142138-46-3
(E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 - 20 °C

2: 83 percent / DDQ, H₂O / CH₂Cl₂

3: 1.) DMSO, oxalyl chloride, 2.) Et₃N

4: SnCl₂ / CH₂Cl₂ / 25 °C

5: 79 percent / NaBH₄ / tetrahydrofuran / 20 h / -78 - 40 °C

With sodium tetrahydroborate; oxalyl dichloride; water; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00075a024

Reference yield:

: 100-39-0
benzyl bromide

: 142138-46-3
(E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / NaH / dimethylformamide / 2 h / -40 - 0 °C

2: 90 percent / 90percent aq. AcOH / methanol / 10 h / 85 °C

3: 99 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 - 20 °C

4: 83 percent / DDQ, H₂O / CH₂Cl₂

5: 1.) DMSO, oxalyl chloride, 2.) Et₃N

6: SnCl₂ / CH₂Cl₂ / 25 °C

7: 79 percent / NaBH₄ / tetrahydrofuran / 20 h / -78 - 40 °C

With sodium tetrahydroborate; oxalyl dichloride; water; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a024