(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

Base Information

Chemical Name:(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester
CAS No.:170889-70-0
Molecular Formula:C₃₇H₅₀O₈
Molecular Weight:622.799
Hs Code.:

(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

Synonyms:(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

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Chemical Property of (E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

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Technology Process of (E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

There total 3 articles about (E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester 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:

: 4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pentanoic acid

: 170889-70-0
(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 2 h, 2.) THF, benzene, reflux, 3 h

2: 1.) LiHMDS, HMPA, PhSeBr, 2.) m-CPBA / 1.) THF, from -78 to -30 deg C, 1 h, 2.) THF, 25 deg C

3: 1.) LiHMDS, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; Phenylselenyl bromide; 2,4,6-trichlorobenzoyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
DOI:10.1021/ja00146a009

Reference yield:

: 162062-39-7
C₃₆H₄₈O₇

: 170889-70-0
(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) LiHMDS, HMPA, PhSeBr, 2.) m-CPBA / 1.) THF, from -78 to -30 deg C, 1 h, 2.) THF, 25 deg C

2: 1.) LiHMDS, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF

With N,N,N,N,N,N-hexamethylphosphoric triamide; Phenylselenyl bromide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
DOI:10.1021/ja00146a009

Reference yield:

: 67-56-1
methanol

: 170889-69-7
C₃₆H₄₆O₇

: 170889-70-0
(E)-4-[(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-2,4a,5a-trimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-pent-3-enoic acid methyl ester

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min, 2.) THF;
DOI:10.1021/ja00146a009