Carbamic acid, 6-2-(acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-3-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-.beta.-D-glucopyranosyloxyhexyl-, phenylmethyl ester

Base Information

• Chemical Name: Carbamic acid, 6-2-(acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-3-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-.beta.-D-glucopyranosyloxyhexyl-, phenylmethyl ester
• CAS No.: 74653-36-4
• Molecular Formula: C39H56 N2 O17
• Molecular Weight: 824.87

Synonyms:Pyrano[3,2-d]-1,3-dioxin,carbamic acid deriv.

Chemical Property of Carbamic acid, 6-2-(acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-3-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-.beta.-D-glucopyranosyloxyhexyl-, phenylmethyl ester

Chemical Property:

• PSA: 228.01000
• LogP: 3.12100

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, 6-2-(acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-3-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-.beta.-D-glucopyranosyloxyhexyl-, phenylmethyl ester

There total 5 articles about Carbamic acid, 6-2-(acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-3-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-.beta.-D-glucopyranosyloxyhexyl-, phenylmethyl ester 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: 61.0%

6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (74653-29-5) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (74653-36-4)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 60 ℃; for 4h;

DOI:10.1016/S0008-6215(00)85520-2

Reference yield:

6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside (62205-57-6) → 6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (74653-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / p-toluenesulfonic acid / dimethylformamide / 12 h / Ambient temperature

2: 61 percent / mercuric cyanide / benzene; nitromethane / 4 h / 60 °C

With mercury(II) cyanide; toluene-4-sulfonic acid; In nitromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0008-6215(00)85520-2

Reference yield:

6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside (62205-56-5,159173-77-0) → 6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (74653-36-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / sodium methoxide / methanol / 24 h

2: 96 percent / p-toluenesulfonic acid / dimethylformamide / 12 h / Ambient temperature

3: 61 percent / mercuric cyanide / benzene; nitromethane / 4 h / 60 °C

With sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; In methanol; nitromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0008-6215(00)85520-2

upstream raw materials:

6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside

6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside

Downstream raw materials:

6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranoside

{6-[(4aR,6R,7R,8R,8aS)-7-Acetylamino-2,2-dimethyl-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-hexyl}-carbamic acid benzyl ester

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