methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

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Chemical Name:methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside
CAS No.:211509-30-7
Molecular Formula:C₄₂H₅₀O₁₄S
Molecular Weight:810.917
Hs Code.:

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

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

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

There total 7 articles about methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 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: 22.0%

: 73045-58-6
methyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside

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

: 211509-30-7
methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 1h;
DOI:10.1021/jo9800356

Reference yield:

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

: 211509-30-7
methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / NH₂NH₂*AcOH / dimethylformamide / 3 h / 60 °C

2: 84 percent / DBU / 0 °C

3: 22 percent / molecular sieves 4 Angstroem, BF₃*OEt₂ / CH₂Cl₂ / 1 h / -20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9800356

Reference yield:

: 100-39-0
benzyl bromide

: 211509-30-7
methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, rt, 1 h

2: (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 0.33 h / Ambient temperature

3: 22 percent / molecular sieves 4 Angstroem, BF₃*OEt₂ / CH₂Cl₂ / 1 h / -20 °C

With ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; water; acetonitrile;
DOI:10.1021/jo9800356