(6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

Base Information

Chemical Name:(6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol
CAS No.:158570-82-2
Molecular Formula:C₃₀H₄₆O₆Si
Molecular Weight:530.777
Hs Code.:

Synonyms:(6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

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Technology Process of (6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

There total 7 articles about (6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-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: 82.0%

: 158535-88-7
2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-erythrose

: 84510-37-2,131433-64-2,131433-65-3
(1S,2E)-1-(tri-n-butylstannyl)-1-(methoxymethoxy)-2-butene

: 158570-82-2
(6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

Guidance literature:: With indium(III) chloride; In ethyl acetate; for 5h; -78 deg C -> room temperature;
DOI:10.1021/jo9640231

Reference yield: 46.0%

: 136981-88-9,131352-13-1,131352-17-5
(Z)-1-(Methoxymethoxy)-3-(tri-n-butylstannyl)-1-butene

: 158535-88-7
2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-erythrose

: 158570-92-4
(2R,3R,4R,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

: 158570-82-2
(6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

: 158570-91-3
(2R,3R,4S,5R,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

: (2S,3R)-2,3-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxymethoxy-3-methyl-cyclopropyl)-butan-1-ol

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2.5h; Yields of byproduct given;
DOI:10.1021/jo00091a034

Reference yield:

: 100-39-0
benzyl bromide

: 158570-82-2
(6E,2R,3R,4S,5S)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 48 percent / Ag₂O / diethyl ether / 20 h / Ambient temperature

2: AlMe₃ / CH₂Cl₂; hexane / 1.) r.t., 15 min, 2.) 0 deg C, 20 min

3: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

4: 94 percent / DIBALH / tetrahydrofuran; toluene / 0.5 h / -78 °C

5: BF₃*OEt₂ / CH₂Cl₂ / 2.5 h / -78 °C

With 1H-imidazole; boron trifluoride diethyl etherate; trimethylaluminum; diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00091a034