2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 81823-04-3
• Molecular Formula: C₄₂H₄₅NO₈S
• Molecular Weight: 723.887

Synonyms:2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

There total 6 articles about 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-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: 89.0%

2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-2-O-p-nitrobenzoyl-β-D-glycopyranoside (81823-03-2) → 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (81823-04-3)

Guidance literature:

With sodium ethanolate; In ethanol; Ambient temperature;

DOI:10.1016/S0008-6215(00)88056-8

Reference yield:

3,4,6-tri-O-benzyl-D-glucopyranose (20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1) → 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (81823-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / Ambient temperature

2: hydrogen chloride / diethyl ether / 24 h / Ambient temperature

3: acetonitrile / 0.25 h / Ambient temperature

4: acetonitrile / 24 h / Ambient temperature; in the dark

5: 89 percent / sodium ethoxide / ethanol / Ambient temperature

With pyridine; hydrogenchloride; sodium ethanolate; In diethyl ether; ethanol; acetonitrile;

DOI:10.1016/S0008-6215(00)88056-8

Reference yield:

2-<4-(p-toluenesulfonamido)-phenyl>ethanol (70274-98-5) → 2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (81823-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 24 h / Ambient temperature; in the dark

2: 89 percent / sodium ethoxide / ethanol / Ambient temperature

With sodium ethanolate; In ethanol; acetonitrile;

DOI:10.1016/S0008-6215(00)88056-8

upstream raw materials:

2-<4-(p-toluenesulfonamido)phenyl>ethyl 3,4,6-tri-O-benzyl-2-O-p-nitrobenzoyl-β-D-glycopyranoside

3,4,6-tri-O-benzyl-D-glucopyranose

2-<4-(p-toluenesulfonamido)-phenyl>ethanol

3,4,6-tri-O-benzyl-2-O-p-nitrobenzoyl-α-D-glucopyranosyl chloride

Downstream raw materials:

N-(4-{2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-phenyl)-4-methyl-benzenesulfonamide

β-D-Glc p-(1->2)-β-D-Glc

4-Nitro-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-{2-[4-(toluene-4-sulfonylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

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