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

Base Information

Chemical Name:(2S,3R,4R,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol
CAS No.:131483-73-3
Molecular Formula:C₃₀H₄₆O₆Si
Molecular Weight:530.777
Hs Code.:

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

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

There total 6 articles about (2S,3R,4R,5S,6E)-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: 99.0%

: 131379-07-2
(2R,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

: 131352-13-1,131352-17-5,136981-88-9
(3R,1Z)-3-(tri-n-butylstannyl)-1-(methoxymethoxy)-1-butenee

: 131483-73-3
(2S,3R,4R,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

Guidance literature:: With magnesium bromide; In dichloromethane; 1.) -23 deg C, 45 min, 2.) -23 deg C to r.t., then r.t., 4.25 h;
DOI:10.1021/jo00091a034

Reference yield: 49.0%

: 131379-07-2
(2R,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

: 131352-13-1,131352-17-5,136981-88-9
(3R,1Z)-3-(tri-n-butylstannyl)-1-(methoxymethoxy)-1-butenee

: 131483-73-3
(2S,3R,4R,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

: 158646-95-8
(2S,3R,4S,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/jo00091a034

Reference yield:

: 77312-71-1
diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate

: 131483-73-3
(2S,3R,4R,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / LiAlH₄

2: 95 percent / n-BuLi / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) 0 deg C, 1 h

3: 93 percent / Dess-Martin reagent / CH₂Cl₂ / 0.33 h / Ambient temperature

4: 99 percent / MgBr₂*OEt₂ / CH₂Cl₂ / 1.) -23 deg C, 45 min, 2.) -23 deg C to r.t., then r.t., 4.25 h

With lithium aluminium tetrahydride; n-butyllithium; Dess-Martin periodane; magnesium bromide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00091a034