p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside
CAS No.:1602921-03-8
Molecular Formula:C₆₁H₆₄O₉S
Molecular Weight:973.24
Hs Code.:

Synonyms:

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Chemical Property of p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

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Technology Process of p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

There total 5 articles about p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-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:

: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-glucopyranoside

: 1363157-69-0
p-methylphenyl 2,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

: 1602921-02-7
p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

: 1602921-03-8
p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-glucopyranoside; With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-formamide; In dichloromethane; at -40 - 20 ℃; for 0.416667h; Molecular sieve;

p-methylphenyl 2,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside; With N,N-dimethyl-formamide; In dichloromethane; at -40 ℃; for 24h; Overall yield = 77 %; Overall yield = 150 mg; Molecular sieve; Inert atmosphere;
DOI:10.1002/ejoc.201400006

Reference yield:

: 69515-91-9
1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose

: 1602921-02-7
p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

: 1602921-03-8
p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

2.1: sodium / methanol / 5 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: N,N-dimethyl-formamide; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.42 h / -40 - 20 °C / Molecular sieve

4.2: 24 h / -40 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium; sodium hydride; N,N-dimethyl-formamide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201400006

Reference yield:

: 61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0
2-deoxy-D-arabino-hexopyranose

: 1602921-02-7
p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

: 1602921-03-8
p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4,6-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; triethylamine / acetonitrile / 4 h / 0 - 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

3.1: sodium / methanol / 5 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C

5.1: N,N-dimethyl-formamide; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.42 h / -40 - 20 °C / Molecular sieve

5.2: 24 h / -40 °C / Molecular sieve; Inert atmosphere

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium; sodium hydride; triethylamine; N,N-dimethyl-formamide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201400006