(3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

Base Information

Chemical Name:(3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol
CAS No.:736141-19-8
Molecular Formula:C₁₈H₂₈O₅
Molecular Weight:324.417
Hs Code.:

Synonyms:(3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

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Chemical Property of (3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

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Technology Process of (3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

There total 5 articles about (3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-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: 85.0%

: 736141-18-7
ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate

: 736141-19-8
(3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; for 1.16667h;
DOI:10.1021/ja0485917

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

: 736141-19-8
(3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

Guidance literature:: Multi-step reaction with 5 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

With 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; 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

: 736141-19-8
(3S,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

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

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

With lithium aluminium tetrahydride; silver(l) oxide; In diethyl ether; toluene;
DOI:10.1021/ja0485917