(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

Base Information

Chemical Name:(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol
CAS No.:866021-85-4
Molecular Formula:C₃₅H₆₆O₆Si₂
Molecular Weight:639.076
Hs Code.:

(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

Synonyms:(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

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Chemical Property of (2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

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Technology Process of (2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

There total 8 articles about (2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol 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:

: 866021-67-2
(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

: 866021-85-4
(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

Guidance literature:: With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -30 ℃;
DOI:10.1021/ol051405x

Reference yield:

: 866021-62-7
((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester

: 866021-85-4
(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: PPh₃ / CH₂Cl₂

2.1: diethyl ether / -78 °C

3.1: LiAlH₄ / diethyl ether / -78 °C

4.1: imidazole; DMAP / dimethylformamide

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: PPh₃ / CH₂Cl₂

6.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

6.3: 87 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

7.1: Me₄NBH(OAc)3; AcOH / acetonitrile / -30 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; ozone; acetic acid; triethylamine; (-)-diisopinocamphenylborane chloride; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol051405x

Reference yield:

: 866021-79-6
[(2R,6S)-6-(2-oxoethyl)tetrahydropyran-2-yl]acetic acid ethyl ester

: 866021-85-4
(2S,3R,5R,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-2-methyloctane-3,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: diethyl ether / -78 °C

2.1: LiAlH₄ / diethyl ether / -78 °C

3.1: imidazole; DMAP / dimethylformamide

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: PPh₃ / CH₂Cl₂

5.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

5.3: 87 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

6.1: Me₄NBH(OAc)3; AcOH / acetonitrile / -30 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; ozone; acetic acid; triethylamine; (-)-diisopinocamphenylborane chloride; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol051405x