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

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Chemical Name: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
CAS No.:146558-08-9
Molecular Formula:C₃₅H₄₂O₁₄S
Molecular Weight:718.776
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 2 articles about 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 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:

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

: 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

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: 3 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