Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester
• CAS No.: 200860-28-2
• Molecular Formula: C₂₁H₂₅NO₁₁
• Molecular Weight: 467.43
• Mol file: 200860-28-2.mol

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester

There total 4 articles about Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-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: 98.0%

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) + phenyl isocyanate (103-71-9) → Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester (200860-28-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In toluene; Ambient temperature;

DOI:10.1016/S0040-4039(97)10393-8

Reference yield:

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) + phenyl isocyanate (103-71-9) → Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester (200860-28-2) + Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester

Guidance literature:

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose; With sodium hydride; In dichloromethane; at 20 ℃; for 1h;

phenyl isocyanate; In dichloromethane; for 0.666667h;

DOI:10.1016/j.carres.2004.10.002

Reference yield:

benzoyl chloride (98-88-4) → Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester (200860-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃ / acetone

2: Heating; Curtius rearrangement

3: 98 percent / 1,4-diazabicyclo<2.2.2>octane / toluene / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; sodium azide; In acetone; toluene;

DOI:10.1016/S0040-4039(97)10393-8

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

phenyl isocyanate

benzoyl chloride

benzoyl azide

Downstream raw materials:

octyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside