Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 220308-32-7
• Molecular Formula: C₂₂H₃₀O₁₂
• Molecular Weight: 486.473
• Mol file: 220308-32-7.mol

Synonyms:

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-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: 61.0%

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-bromo-2-methyl-3-oxo-1-prop-2-ynyloxy-butoxy)-tetrahydro-pyran-3-yl ester (220308-28-1) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester (220308-32-7)

Guidance literature:

With N-ethylpiperidine hypophosphite; 2,2'-azobis(isobutyronitrile); In toluene; for 1h; Heating;

DOI:10.1039/a807930g

Reference yield:

(E)-3-methyl-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one (122080-17-5) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester (220308-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / NBS

2: 61 percent / 1-ethylpiperidinium hypophosphite, AIBN / toluene / 1 h / Heating

With N-Bromosuccinimide; N-ethylpiperidine hypophosphite; 2,2'-azobis(isobutyronitrile); In toluene;

DOI:10.1039/a807930g

Reference yield: 79.0%

methanol (67-56-1) + Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-4-methylene-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-3-yl ester (220308-32-7) → 1-((S)-2-Methoxy-3-methyl-4-methylene-tetrahydro-furan-3-yl)-ethanone (220350-85-6,220308-44-1)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1039/a807930g

upstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-bromo-2-methyl-3-oxo-1-prop-2-ynyloxy-butoxy)-tetrahydro-pyran-3-yl ester

(E)-3-methyl-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one

Downstream raw materials:

1-((S)-2-Methoxy-3-methyl-4-methylene-tetrahydro-furan-3-yl)-ethanone