methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside
CAS No.:146558-07-8
Molecular Formula:C₃₅H₄₂O₁₄S
Molecular Weight:718.776
Hs Code.:

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

There total 4 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-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: 70.0%

: 76419-48-2
methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

: 146558-06-7
2,3,4,6-tetra-O-acetyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

: 146558-08-9
3,4,6-tri-O-acetyl-1,2-(methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-2-yl)-α-D-5'-thio-α-D-glucopyranose orthoacetate

: 146558-07-8
methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

: 146609-14-5
Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester

Guidance literature:: With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -78 ℃; for 3.5h;
DOI:10.1016/0040-4039(93)88013-9

Reference yield: 33.0%

: 76419-48-2
methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

: 161687-10-1
phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-5-thio-α-D-glucopyranoside

: 84039-46-3
1,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranoside

: 146558-07-8
methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: With 4 A molecular sieve; nitrosonium tetrafluoroborate; In dichloromethane; at -30 - 0 ℃; for 2.5h;
DOI:10.1016/S0957-4166(00)80386-9

Reference yield:

: 10470-80-1
1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose

: 146558-07-8
methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / hydrazine acetate / dimethylformamide / 3 h

2: 81 percent / potassium carbonate / CH₂Cl₂ / 24 h

3: 68 percent / triethylsilyl triflate, 4 A molecular sieves / CH₂Cl₂ / 6.5 h / -78 °C

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)80386-9