4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside
• CAS No.: 572910-57-7
• Molecular Formula: C₃₃H₃₈N₄O₁₂S
• Molecular Weight: 714.75
• Mol file: 572910-57-7.mol

Synonyms:4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside

Chemical Property of 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside

There total 4 articles about 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-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: 88.0%

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside (596814-32-3) + 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranose (596814-34-5) → 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside (572910-57-7)

Guidance literature:

3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranose; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/S0008-6215(03)00149-6

Reference yield:

(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(((benzyloxy)carbonyl)amino)-6-chlorotetrahydro-2H-pyran-3,4-diyl diacetate (31281-51-3) → 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside (572910-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 47 percent / acetone / 7 h / Heating

2.1: 81 percent / Na₂SO₃; H₂O / acetone / 22 h / 20 °C

3.1: NaH (55 percent) / dimethylformamide / 0 - 20 °C

3.2: 88 percent / dimethylformamide / 1 h / 20 °C

With water; sodium hydride; sodium sulfite; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(03)00149-6

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) → 4-S-(3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-thio-β-D-glucopyranoside (572910-57-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / pyridine / CH₂Cl₂ / -15 - 20 °C

2.1: NaNO₂ / dimethylformamide / 20 h / 20 °C

2.2: 68 percent / H₂O / CH₂Cl₂

3.1: 94 percent / pyridine / CH₂Cl₂ / -15 - 20 °C

4.1: NaH (55 percent) / dimethylformamide / 0 - 20 °C

4.2: 88 percent / dimethylformamide / 1 h / 20 °C

With pyridine; sodium hydride; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(03)00149-6

upstream raw materials:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside

3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranose

(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(((benzyloxy)carbonyl)amino)-6-chlorotetrahydro-2H-pyran-3,4-diyl diacetate

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose