O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

Base Information

Chemical Name:O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose
CAS No.:1350618-93-7
Molecular Formula:C₃₄H₄₂O₁₄S
Molecular Weight:706.765
Hs Code.:

Synonyms:O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

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Chemical Property of O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

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Technology Process of O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

There total 4 articles about O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose 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: 58.0%

: 1350618-73-3
O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-1,6-anhydro-3,4-di-O-benzyl-β-D-glucopyranose

: 1350618-93-7
O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

Guidance literature:: With hexamethyldisilathiane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 50 ℃; stereospecific reaction; Inert atmosphere; Molecular sieve;
DOI:10.1021/jo202069y

Reference yield:

: 10548-46-6
1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose

: 1350618-93-7
O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: tin(IV) chloride / dichloromethane / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -50 °C / Inert atmosphere; Molecular sieve

3: hexamethyldisilathiane; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 50 °C / Inert atmosphere; Molecular sieve

With hexamethyldisilathiane; trimethylsilyl trifluoromethanesulfonate; tin(IV) chloride; In dichloromethane; 2: Schmidt glycosylation;
DOI:10.1021/jo202069y

Reference yield:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 1350618-93-7
O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: ferric perchlorate / acetonitrile / 6 h / Inert atmosphere; Reflux

2: tin(IV) chloride / dichloromethane / Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -50 °C / Inert atmosphere; Molecular sieve

4: hexamethyldisilathiane; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 50 °C / Inert atmosphere; Molecular sieve

With hexamethyldisilathiane; trimethylsilyl trifluoromethanesulfonate; ferric perchlorate; tin(IV) chloride; In dichloromethane; acetonitrile; 3: Schmidt glycosylation;
DOI:10.1021/jo202069y