[(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

Base Information

Chemical Name:[(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane
CAS No.:921770-98-1
Molecular Formula:C₃₃H₄₈O₅Si
Molecular Weight:552.827
Hs Code.:

Synonyms:[(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

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Chemical Property of [(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

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Technology Process of [(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

There total 9 articles about [(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane 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: 91.0%

: 921770-97-0
(1R,2R,3R,5S)-3-(tert-butyl-dimethylsilanyloxy)-5-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentane-1,2-diol

: 100-39-0
benzyl bromide

: 921770-98-1
[(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

Guidance literature:: (1R,2R,3R,5S)-3-(tert-butyl-dimethylsilanyloxy)-5-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentane-1,2-diol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

benzyl bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/jo061717t

Reference yield:

: 763105-46-0
(S)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-cyclopent-2-enol

: 921770-98-1
[(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / Jones reagent / acetone / 0.5 h / 0 °C

2.1: 79 percent / LiAlH₄ / diethyl ether / 1 h / -60 °C

3.1: 96 percent / triethylamine; DMAP; imidazole / CH₂Cl₂ / 18 h / 20 °C

4.1: 96 percent / N-methyl-morpholine N-oxide monohydrate / OsO₄ / acetone; H₂O / 14 h / 20 °C

5.1: NaH / tetrahydrofuran / 2 h / 20 °C

5.2: 91 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; jones reagent; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/jo061717t

Reference yield:

: 921770-86-7
(4S)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-2-en-1-one

: 921770-98-1
[(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 79 percent / LiAlH₄ / diethyl ether / 1 h / -60 °C

2.1: 96 percent / triethylamine; DMAP; imidazole / CH₂Cl₂ / 18 h / 20 °C

3.1: 96 percent / N-methyl-morpholine N-oxide monohydrate / OsO₄ / acetone; H₂O / 14 h / 20 °C

4.1: NaH / tetrahydrofuran / 2 h / 20 °C

4.2: 91 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/jo061717t