(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

Base Information

Chemical Name:(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran
CAS No.:863604-38-0
Molecular Formula:C₃₇H₆₂O₃Si₂
Molecular Weight:611.068
Hs Code.:

Synonyms:(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

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Chemical Property of (2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

Chemical Property:

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Technology Process of (2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

There total 3 articles about (2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran 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:

: 863604-37-9
(3S,4R)-3-(dimethylphenylsilanyl)-4-(tert-butyldimethylsilanyloxy)tridec-1-ene

: 60656-87-3
benzyloxyacetoaldehyde

: 863604-38-0
(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

: (2R,3S,5S)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

Guidance literature:: With 4 A molecular sieve; tin(IV) chloride; In dichloromethane; at -45 ℃; for 20h; Title compound not separated from byproducts;
DOI:10.1021/ja051986l

Reference yield:

: 112-44-7
undecylaldehyde

: 60656-87-3
benzyloxyacetoaldehyde

: 18162-48-6
tert-butyldimethylsilyl chloride

: 327628-32-0
[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

: 863604-38-0
(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

Guidance literature:: undecylaldehyde; [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 4h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 48h;

benzyloxyacetoaldehyde; With tin(IV) chloride; In dichloromethane; at -45 ℃; for 20h;
DOI:10.1021/jo0511290

Reference yield:

: 18001-18-8
allyldimethylphenylsilane

: 863604-38-0
(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / -78 - -45 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

2.2: imidazole / dimethylformamide / 48 h / 50 °C

2.3: 1.2 g / SnCl₄ / CH₂Cl₂ / 20 h / -45 °C

With n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; In tetrahydrofuran; hexane;
DOI:10.1021/jo0511290