(2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

Base Information

Chemical Name:(2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane
CAS No.:736141-20-1
Molecular Formula:C₂₄H₄₂O₅Si
Molecular Weight:438.68
Hs Code.:

Synonyms:(2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

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Chemical Property of (2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

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Technology Process of (2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

There total 5 articles about (2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane 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:

: 736140-94-6
(2E)-(5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-2-heptene-1-one

: 736141-20-1
(2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

Guidance literature:: Multi-step reaction with 6 steps

1: 853 mg / Sm(O-iPr)3; (R)-H₈-BINOL; cumene hydroperoxide / toluene; tetrahydrofuran / 0.67 h / 25 °C

2: 94.5 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 0.25 h / 25 °C

3: 92 percent / EtSLi / ethanol / 0.67 h / 25 °C

4: 93 percent / Ag₂O / toluene / 36 h / 45 °C

5: 85 percent / LiAlH₄ / diethyl ether / 1.17 h

6: 97 percent / imidazole / CH₂Cl₂ / 0.83 h / 25 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; Cumene hydroperoxide; diphenyl diselenide; samarium(III) isopropoxide; lithium thioethoxide; acetic acid; (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol; silver(l) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/ja0485917

Reference yield:

: 627546-49-0
ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

: 736141-20-1
(2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / Ag₂O / toluene / 36 h / 45 °C

2: 85 percent / LiAlH₄ / diethyl ether / 1.17 h

3: 97 percent / imidazole / CH₂Cl₂ / 0.83 h / 25 °C

With 1H-imidazole; lithium aluminium tetrahydride; silver(l) oxide; In diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja0485917

Reference yield:

: 627546-46-7
(2S,3R,5R,6R)-7-benzyloxy-trans-2,3-epoxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-1-heptanone

: 736141-20-1
(2R,3R,5S)-1-benzyloxy-7-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2,3-O-isopropylidene-5-methoxyheptane

Guidance literature:: Multi-step reaction with 5 steps

1: 94.5 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 0.25 h / 25 °C

2: 92 percent / EtSLi / ethanol / 0.67 h / 25 °C

3: 93 percent / Ag₂O / toluene / 36 h / 45 °C

4: 85 percent / LiAlH₄ / diethyl ether / 1.17 h

5: 97 percent / imidazole / CH₂Cl₂ / 0.83 h / 25 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; diphenyl diselenide; lithium thioethoxide; acetic acid; silver(l) oxide; In diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/ja0485917