[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] acetate

Base Information

• Chemical Name: [(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] acetate
• CAS No.: 3554-95-8
• Molecular Formula: C₁₇H₂₃NO₇
• Molecular Weight: 353.372
• DSSTox Substance ID: DTXSID201152258
• Nikkaji Number: J2.774.475C
• Mol file: 3554-95-8.mol

Synonyms:3554-95-8;DTXSID201152258;alpha-D-Galactopyranoside, phenylmethyl 2-(acetylamino)-2-deoxy-, 3-acetate;(2S,3R,4R,5R,6R)-3-acetamido-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl acetate

Chemical Property of [(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] acetate

Chemical Property:

• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 353.14745207
• Heavy Atom Count: 25
• Complexity: 452

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCC2=CC=CC=C2)CO)O)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@@H]1OCC2=CC=CC=C2)CO)O)OC(=O)C

Technology Process of [(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] acetate

There total 1 articles about [(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] acetate 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:

→ benzyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside (3554-95-8)

Guidance literature:

Benzyl-2-acetamido-4,6-O-benzyliden-2-deoxy-α-D-galactopyranosid, 1) Acetanhydrid, Py., 2) Rueckstand mit 60percent wss. Eg. (100grad, 30 Min.);

DOI:10.1021/jo01017a078

Reference yield: 85.0%

benzyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside (3554-95-8) + 2-phthalimido-2,3-dideoxy-3-fluoro-4,6-di-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (1193357-22-0) → benzyl 6-O-[2-phthalimido-2,3-dideoxy-3-fluoro-4,6-di-O-acetyl-β-D-glucopyranosyl]-2-acetamido-2-deoxy-3-O-acetyl-α-D-galactopyranoside (1193357-30-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -70 - -65 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2009.07.089

Reference yield: 85.0%

benzyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside (3554-95-8) + 2-(2,2,2-trichloroethoxycarbonylamino)-2,4-dideoxy-4-fluoro-3,6-di-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (1193357-13-9) → benzyl 6-O-[2-(2,2,2-trichloroethoxycarbonylamino)-2,4-dideoxy-4-fluoro-3,6-di-O-acetyl-β-D-glucopyranosyl]-2-acetamido-2-deoxy-3-O-acetyl-α-D-galactopyranoside (1193357-25-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -70 - -65 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2009.07.089

Downstream raw materials:

benzyl 2-acetamido-6-O-(2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-α-D-galactopyranoside

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside

Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((2R,3R,4R,5R,6S)-4-acetoxy-5-acetylamino-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethoxy)-6-acetoxymethyl-tetrahydro-pyran-4-yl ester

C₄₈H₅₈N₂O₂₂