Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 77611-20-2
• Molecular Formula: C₃₁H₃₅NO₇
• Molecular Weight: 533.621
• Mol file: 77611-20-2.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl 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: 80.0%

C29H31N3O6 + acetic anhydride (108-24-7) → Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (77611-20-2)

Guidance literature:

C₂₉H₃₁N₃O₆; With ammonium tetrathiomonomolybdate; In ethanol; acetonitrile; at 20 ℃; for 10h;

acetic anhydride; With triethylamine; In dichloromethane;

DOI:10.1039/c7ra08637g

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (77611-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilylazide; trimethylsilyl trifluoromethanesulfonate / -30 °C

2: ammonium tetrathiomonomolybdate / ethanol; acetonitrile / 10 h / 20 °C

With ammonium tetrathiomonomolybdate; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; In ethanol; acetonitrile;

DOI:10.1039/c7ra08637g

Reference yield:

acetic anhydride (108-24-7) + 2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine (77611-19-9) → Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (77611-20-2)

Guidance literature:

Multistep reaction;

DOI:10.1021/jo00328a045

upstream raw materials:

acetic anhydride

2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine

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