alpha-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 3,4,6-triacetate

Base Information

• Chemical Name: alpha-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 3,4,6-triacetate
• CAS No.: 7772-76-1
• Molecular Formula: NH₄H₂PO₄
• Molecular Weight: 453.446
• European Community (EC) Number: 616-489-4
• DSSTox Substance ID: DTXSID501122828
• Mol file: 7772-76-1.mol

Synonyms:7772-76-1;IREJBJSFPQKDNH-WAPOTWQKSA-N;DTXSID501122828;alpha-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 3,4,6-triacetate

Chemical Property of alpha-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 3,4,6-triacetate

Chemical Property:

• PSA: 135.69000
• LogP: 1.47010
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 453.16349606
• Heavy Atom Count: 32
• Complexity: 663

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC)NC(=O)OCC2=CC=CC=C2)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC)NC(=O)OCC2=CC=CC=C2)OC(=O)C)OC(=O)C

Technology Process of alpha-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 3,4,6-triacetate

There total 4 articles about alpha-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 3,4,6-triacetate 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: 28.0%

methyl 2-benzyloxycarbonylamino-2-deoxy-α/β-D-glucopyranoside (57089-81-3) + acetic anhydride (108-24-7) → 3,4,6-tri-O-acetyl-2--2-deoxy-1-O-methyl-β-D-glucopyranoside (31281-57-9) + methyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (7772-76-1)

Guidance literature:

With dmap; In pyridine; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2020.127400

Reference yield:

→ methyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (7772-76-1)

Guidance literature:

With pyridine; acetic anhydride;

DOI:10.1021/ja01575a058

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → methyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (7772-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol; water / 24 h / 40 °C

2: dmap / pyridine / 0 - 20 °C

With hydrogenchloride; dmap; In pyridine; methanol; water;

DOI:10.1016/j.bmcl.2020.127400

upstream raw materials:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

methyl 2-benzyloxycarbonylamino-2-deoxy-α/β-D-glucopyranoside

acetic anhydride

Refernces