(3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

Base Information

Chemical Name:(3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene
CAS No.:88392-86-3
Molecular Formula:C₂₇H₃₂O₆
Molecular Weight:452.547
Hs Code.:

Synonyms:(3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

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Chemical Property of (3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

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Technology Process of (3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

There total 11 articles about (3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene 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: 86.0%

: 88392-85-2
(2R,3S,4R,4aR,5S,6S,8aS)-4,5-Bis-benzyloxy-2-((E)-2-[1,3]dioxolan-2-yl-vinyl)-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

: 88392-86-3
(3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol;
DOI:10.1021/ja00315a046

Reference yield: 70.0%

: 67-56-1
methanol

: 88392-85-2
(2R,3S,4R,4aR,5S,6S,8aS)-4,5-Bis-benzyloxy-2-((E)-2-[1,3]dioxolan-2-yl-vinyl)-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

: 88392-86-3
(3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

Guidance literature:: With pyridinium p-toluenesulfonate; at 20 ℃; for 20h;
DOI:10.1021/jo00229a014

Reference yield:

: 88412-17-3
Acetic acid (2R,3S,4R,4aR,8aS)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-yl ester

: 88392-86-3
(3S,4S,4aR,6R,8aR,9aS,10R,10aS)-4,10-Bis-benzyloxy-6-methoxy-3-methyl-3,4,4a,6,8a,9a,10,10a-octahydro-2H-1,5,9-trioxa-anthracene

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / MCPBA

2: 97 percent

3: 1.) oxidation; 2.) reduction

4: hydrolysis

6: 96 percent / oxidation

8: 86 percent / PPTS / methanol

With pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; In methanol;
DOI:10.1021/ja00315a046