allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

Base Information

Chemical Name:allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside
CAS No.:171614-54-3
Molecular Formula:C₃₇H₄₆O₁₅
Molecular Weight:730.763
Hs Code.:

Synonyms:allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

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Chemical Property of allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

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Technology Process of allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

There total 16 articles about allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside 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: 77.0%

: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((4aR,6R,7R,8S,8aR)-6-allyloxy-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester

: 171614-54-3
allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

Guidance literature:: With triethylsilane; In trifluoroacetic acid; at 0 ℃;
DOI:10.1021/jo00125a005

Reference yield: 77.0%

: 200003-48-1
allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

: 171614-54-3
allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

Guidance literature:: With triethylsilane; trifluoroacetic acid; at 0 ℃;
DOI:10.1016/0040-4039(96)00177-3

Reference yield:

: 13322-90-2
3,4,6-tri-O-benzoyl-D-glucal

: 171614-54-3
allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / 4-methylmorpholine N-oxide / osmium tetraoxide / acetone; H₂O; 2-methyl-propan-2-ol / 120 h

2: 88 percent / thionyl diimidazole / tetrahydrofuran / 0.33 h / -20 °C

3: 76 percent / 3 Angstroem molecular sieves / ytterbium(III) triflate / toluene / 12 h / 100 °C

4: 95 percent / trifluoromethane sulfonic acid / CH₂Cl₂; cyclohexane / 4 h / 20 °C

5: 91 percent / sodium methoxide / methanol / 12 h

6: 77 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 50 °C / reduced pressure

7: 85 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂

8: 77 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 3.5 h / 0 °C

With triethylsilane; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; thionyl diimidazole; sodium methylate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; osmium(VIII) oxide; ytterbium(III) triflate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1: Oxidation / 2: Cyclization / 3: glycosylation / 4: Etherification / 5: methanolysis / 6: Cyclization / 7: Schmidt glycosylation / 8: Ring cleavage;
DOI:10.1016/S0040-4020(97)01024-7