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

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-benzyloxymethoxy-propoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 112146-71-1
• Molecular Formula: C₂₈H₃₈O₁₃
• Molecular Weight: 582.602
• Mol file: 112146-71-1.mol

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

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

There total 3 articles about Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-benzyloxymethoxy-propoxy)-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: 92.0%

Benzyloxymethyl chloride (3587-60-8) + Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-hydroxy-propoxy)-tetrahydro-pyran-4-yl ester (112146-67-5) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-benzyloxymethoxy-propoxy)-tetrahydro-pyran-4-yl ester (112146-71-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 40 ℃; for 3h;

DOI:10.1016/S0040-4039(01)81041-8

Reference yield:

(R)-3-allyloxypropane-1,2-diol (123-34-2,73485-54-8,90940-93-5,55941-86-1) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-benzyloxymethoxy-propoxy)-tetrahydro-pyran-4-yl ester (112146-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Ag₂CO₃ / CH₂Cl₂ / -10 °C

2: 92 percent / N,N-diisopropylethylamine (DIPEA) / acetonitrile / 3 h / 40 °C

With N-ethyl-N,N-diisopropylamine; silver carbonate; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)81041-8

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-benzyloxymethoxy-propoxy)-tetrahydro-pyran-4-yl ester (112146-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Ag₂CO₃ / CH₂Cl₂ / -10 °C

2: 92 percent / N,N-diisopropylethylamine (DIPEA) / acetonitrile / 3 h / 40 °C

With N-ethyl-N,N-diisopropylamine; silver carbonate; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)81041-8

upstream raw materials:

Benzyloxymethyl chloride

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

(R)-3-allyloxypropane-1,2-diol

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-{(R)-2-benzyloxymethoxy-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-propoxy}-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester

Succinic acid mono-((R)-2-benzyloxymethoxy-3-{(2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-2-yloxy}-propyl) ester

Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-{(S)-2-benzyloxymethoxy-3-[((E)-propenyl)oxy]-propoxy}-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-((S)-2-benzyloxymethoxy-3-hydroxy-propoxy)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester