Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester
• CAS No.: 625108-33-0
• Molecular Formula: C₃₃H₄₁N₃O₁₇
• Molecular Weight: 751.698

Synonyms:Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

Chemical Property of Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

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Technology Process of Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

There total 3 articles about Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl 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: 76.0%

acetic anhydride (108-24-7) + C37H49N3O13 (625108-32-9) → Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (625108-33-0)

Guidance literature:

C₃₇H₄₉N₃O₁₃; With ethylene glycol; (+)-10-camphorsulfonic acid; In acetonitrile; at 20 ℃; for 14h;

acetic anhydride; With pyridine; at 20 ℃; for 16h;

DOI:10.1016/S0968-0896(03)00154-8

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride (67817-20-3) → Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (625108-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 58 percent / 2,6-diisopropyl-4-methylpyridine; silver triflate / CH₂Cl₂

2.1: (+)-camphorsulfonic acid; ethylene glycol / acetonitrile / 14 h / 20 °C

2.2: 76 percent / pyridine / 16 h / 20 °C

With diisopropyl-2,6-methyl-4-pyridine; silver trifluoromethanesulfonate; ethylene glycol; (+)-10-camphorsulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0968-0896(03)00154-8

Reference yield:

6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-1-L-myo-inositol (116907-54-1) → Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (625108-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 58 percent / 2,6-diisopropyl-4-methylpyridine; silver triflate / CH₂Cl₂

2.1: (+)-camphorsulfonic acid; ethylene glycol / acetonitrile / 14 h / 20 °C

2.2: 76 percent / pyridine / 16 h / 20 °C

With diisopropyl-2,6-methyl-4-pyridine; silver trifluoromethanesulfonate; ethylene glycol; (+)-10-camphorsulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0968-0896(03)00154-8

upstream raw materials:

acetic anhydride

C₃₇H₄₉N₃O₁₃

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride

6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-1-L-myo-inositol

Downstream raw materials:

N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-((1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentahydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl]-acetamide

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