4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

Base Information

Chemical Name:4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester
CAS No.:78880-54-3
Molecular Formula:C₄₂H₄₂O₈
Molecular Weight:674.791
Hs Code.:

Synonyms:4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

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Chemical Property of 4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

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Technology Process of 4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

There total 4 articles about 4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic 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: 72.0%

: 74808-09-6
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 78880-54-3
4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

Guidance literature:: With pyrylium tetrafluoroborate; In diethyl ether; at 23 ℃; for 3h; diastereoselective reaction; Sealed tube;
DOI:10.1002/anie.202115394

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 78880-54-3
4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 24 h / 20 °C / Inert atmosphere

2: pyrylium tetrafluoroborate / diethyl ether / 3 h / 23 °C / Sealed tube

With pyrylium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; dichloromethane;
DOI:10.1002/anie.202115394

Reference yield:

: 6564-72-3
2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 78880-54-3
4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

: 78880-54-3
4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester

Guidance literature:: With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride; Multistep reaction; 1.) CH₂Cl₂, -10 deg C, 0.5 h, 2.) CH₂Cl₂, 0 deg C, 3 h;
DOI:10.1246/bcsj.54.1895