Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 191613-39-5
• Molecular Formula: C₂₃H₃₂N₂O₉
• Molecular Weight: 480.515
• Mol file: 191613-39-5.mol

Synonyms:Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-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:

N-acetyl-D-galactosamine (72-87-7,1136-42-1,1136-44-3,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4,6082-29-7) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester (191613-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / BF₃*Et₂O

2: 94 percent / pyridine

3: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -76 deg C, 10 min

4: NaBH₃CN / tetrahydrofuran / Ambient temperature

With pyridine; dimethylsulfide; boron trifluoride diethyl etherate; sodium cyanoborohydride; ozone; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)00703-X

Reference yield:

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide (64650-83-5) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester (191613-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -76 deg C, 10 min

3: NaBH₃CN / tetrahydrofuran / Ambient temperature

With pyridine; dimethylsulfide; sodium cyanoborohydride; ozone; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)00703-X

Reference yield:

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside (117299-90-8) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-benzylamino-ethoxy)-tetrahydro-pyran-4-yl ester (191613-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -76 deg C, 10 min

2: NaBH₃CN / tetrahydrofuran / Ambient temperature

With dimethylsulfide; sodium cyanoborohydride; ozone; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)00703-X

upstream raw materials:

N-acetyl-D-galactosamine

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside

Downstream raw materials:

C₄₈H₆₈N₄O₂₃

C₄₄H₆₀N₄O₂₃

{Benzyloxycarbonyl-[2-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethyl]-amino}-acetic acid tert-butyl ester

{Benzyloxycarbonyl-[2-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethyl]-amino}-acetic acid