(4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

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Chemical Name:(4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol
CAS No.:915106-60-4
Molecular Formula:C₄₅H₆₈O₅Si₂
Molecular Weight:745.203
Hs Code.:

Synonyms:(4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

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Chemical Property of (4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

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Technology Process of (4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

There total 4 articles about (4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-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: 69.0%

: 915106-48-8
(R)-4-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-butyraldehyde

: 1730-25-2
allylmagnesium bromide

: 915106-60-4
(4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

Guidance literature:: allylmagnesium bromide; With (-)-B-methoxydiisopinocampheylborane; In diethyl ether; at -78 - 20 ℃; for 1h;

(R)-4-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-butyraldehyde; In diethyl ether; at -78 ℃; for 2.5h;
DOI:10.1021/ol0620904

Reference yield:

: 915106-70-6
(S)-4-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol

: 915106-60-4
(4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / NaHCO₃; Dess-Martin periodinane / tetrahydrofuran / 1.5 h / 20 °C

2.1: (-)-(IPC)2BOMe / diethyl ether / 1 h / -78 - 20 °C

2.2: 69 percent / diethyl ether / 2.5 h / -78 °C

With sodium hydrogencarbonate; Dess-Martin periodane; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; diethyl ether; 2.2: Brown's allylation;
DOI:10.1021/ol0620904

Reference yield:

: 915106-69-3
(R)-4-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

: 915106-60-4
(4S,6S)-7-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / Super Hydride / tetrahydrofuran / 0.28 h / -78 °C

2.1: 90 percent / NaHCO₃; Dess-Martin periodinane / tetrahydrofuran / 1.5 h / 20 °C

3.1: (-)-(IPC)2BOMe / diethyl ether / 1 h / -78 - 20 °C

3.2: 69 percent / diethyl ether / 2.5 h / -78 °C

With lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; diethyl ether; 3.2: Brown's allylation;
DOI:10.1021/ol0620904