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

Base Information

Chemical Name:(2S,3R,5R,6R)-7-benzyloxy-trans-2,3-epoxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-1-heptanone
CAS No.:627546-46-7
Molecular Formula:C₂₁H₂₅NO₅
Molecular Weight:371.433
Hs Code.:

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

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Chemical Property of (2S,3R,5R,6R)-7-benzyloxy-trans-2,3-epoxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-1-heptanone

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Technology Process of (2S,3R,5R,6R)-7-benzyloxy-trans-2,3-epoxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-1-heptanone

There total 4 articles about (2S,3R,5R,6R)-7-benzyloxy-trans-2,3-epoxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-1-heptanone 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

: 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

Guidance literature:: With Cumene hydroperoxide; 4 A molecular sieve; (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol; samarium(III) isopropoxide; Triphenylphosphine oxide; In tetrahydrofuran; toluene; at 25 ℃; for 0.7h;
DOI:10.1002/anie.200352509

Reference yield:

: 54582-33-1
1,1'-carbonyldiimidazole

: 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

Guidance literature:: Multi-step reaction with 3 steps

1.1: PhLi / tetrahydrofuran; diethyl ether / 1 h / 25 °C

1.2: 98 percent / tetrahydrofuran; diethyl ether / 25 °C

2.1: 86 percent / toluene / 36 h / 65 °C

3.1: 853 mg / Sm(O-iPr)3; (R)-H₈-BINOL; cumene hydroperoxide / toluene; tetrahydrofuran / 0.67 h / 25 °C

With Cumene hydroperoxide; samarium(III) isopropoxide; phenyllithium; (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol; In tetrahydrofuran; diethyl ether; toluene; 2.1: Wittig olefination;
DOI:10.1021/ja0485917

Reference yield:

: 627546-31-0
1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / toluene / 36 h / 65 °C

2: 853 mg / Sm(O-iPr)3; (R)-H₈-BINOL; cumene hydroperoxide / toluene; tetrahydrofuran / 0.67 h / 25 °C

With Cumene hydroperoxide; samarium(III) isopropoxide; (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol; In tetrahydrofuran; toluene; 1: Wittig olefination;
DOI:10.1021/ja0485917