Acetic acid (2S,3S,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 224629-12-3
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.422
• Mol file: 224629-12-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 1 articles about Acetic acid (2S,3S,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-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: 83.0%

acetic anhydride (108-24-7) + (1R,2S,3R,4S)-3,4-Bis-benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane → Acetic acid (2S,3S,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-tetrahydro-pyran-3-yl ester (224629-12-3)

Guidance literature:

With triethylsilyl trifluoromethyl sulfonate; at -78 - -5 ℃; for 0.5h;

DOI:10.1016/S0957-4166(99)00011-7

Reference yield: 90.0%

Acetic acid (2S,3S,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-tetrahydro-pyran-3-yl ester (224629-12-3) + allyl-trimethyl-silane (762-72-1) → Acetic acid (2S,3R,4R,5S,6R)-6-acetoxymethyl-2-allyl-4-benzyloxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 41h;

DOI:10.1016/S0957-4166(99)00011-7

Reference yield:

Acetic acid (2S,3S,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-tetrahydro-pyran-3-yl ester (224629-12-3) → ((3R,4R,5S,6R)-3-Acetoxy-6-acetoxymethyl-4-benzyloxy-5-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / BF₃*Et₂O / acetonitrile / 41 h / 0 °C

2: 74 percent / O₃ / CH₂Cl₂ / 5 h / -78 °C

With boron trifluoride diethyl etherate; ozone; In dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(99)00011-7

upstream raw materials:

acetic anhydride