(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester
CAS No.:273926-00-4
Molecular Formula:C₃₅H₃₈O₇
Molecular Weight:570.683
Hs Code.:

Synonyms:(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

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Chemical Property of (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

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Technology Process of (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

There total 2 articles about (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl 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: 95.0%

: 273925-99-8
(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(prop-2-ynyl)-tetrahydro-pyran-3-ol

: 623-47-2
propynoic acid ethyl ester

: 273926-00-4
(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane;
DOI:10.1021/ol0000408

Reference yield:

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 273926-00-4
(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi

1.2: 72 percent / -50 - 20 °C

2.1: 95 percent / N-methylmorpholine / CH₂Cl₂

With 4-methyl-morpholine; n-butyllithium; In dichloromethane; 1.1: Transmetallation / 1.2: Ring cleavage / 2.1: Hetero-Michael addition;
DOI:10.1021/ol0000408

Reference yield: 71.0%

: 273926-00-4
(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester

: ((2S,4aS,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-3-methylene-octahydro-pyrano[3,2-b]pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 12h;

With toluene-4-sulfonic acid; In dichloromethane; for 1.5h; Further stages.;
DOI:10.1021/ol0000408