3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside
• CAS No.: 89023-84-7
• Molecular Formula: C₄₀H₃₉NO₁₁S₂
• Molecular Weight: 773.882

Synonyms:3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside

Chemical Property of 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside

Chemical Property:

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Technology Process of 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside

There total 2 articles about 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside 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: 86.0%

potassium benzylxanthate (2720-79-8) + 2,3-epoxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside (89023-80-3) → 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside (89023-84-7)

Guidance literature:

With ammonium chloride; In ethanol; water; for 0.5h; Ambient temperature;

DOI:10.1016/0008-6215(83)88480-8

Reference yield:

allyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside (89023-79-0) → 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside (89023-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 3-chloroperoxybenzoic acid / benzene / 1.5 h / Heating

2: 86 percent / NH₄Cl / ethanol; H₂O / 0.5 h / Ambient temperature

With ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In ethanol; water; benzene;

DOI:10.1016/0008-6215(83)88480-8

Reference yield: 81.0%

3,4-dihydro-2H-pyran (110-87-2) + 3-(benzyloxythiocarbonyl)thio-2-hydroxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside (89023-84-7) → 3-(benzyloxythiocarbonyl)thio-2-O-(tetrahydropyran-2-yl)propyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside (89023-85-8)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; for 0.25h; Ambient temperature;

DOI:10.1016/0008-6215(83)88480-8

upstream raw materials:

potassium benzylxanthate

2,3-epoxypropyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside

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

Downstream raw materials:

3-(benzyloxythiocarbonyl)thio-2-O-(tetrahydropyran-2-yl)propyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside

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