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

Base Information

Chemical Name:p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-3-(2-naphthylmethyl)-1-thio-β-D-galactopyranoside
CAS No.:1602921-06-1
Molecular Formula:C₅₈H₅₈O₉S
Molecular Weight:931.159
Hs Code.:

Synonyms:p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-3-(2-naphthylmethyl)-1-thio-β-D-galactopyranoside

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

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

There total 5 articles about p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-3-(2-naphthylmethyl)-1-thio-β-D-galactopyranoside 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: 75.0%

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

: 1333393-34-2
C₃₁H₃₀O₅S

: 1602921-06-1
p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-3-(2-naphthylmethyl)-1-thio-β-D-galactopyranoside

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;

C₃₁H₃₀O₅S; With N,N-dimethyl-formamide; In dichloromethane; at -40 ℃; for 20h; Molecular sieve; Inert atmosphere;
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

: 1602921-06-1
p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-3-(2-naphthylmethyl)-1-thio-β-D-galactopyranoside

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: 20 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

Reference yield:

: C₁₉H₂₄O₇S

: 1602921-06-1
p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-3-(2-naphthylmethyl)-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium / methanol / 5 h / 20 °C

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

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

3.2: 20 h / -40 °C / Molecular sieve; Inert atmosphere

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