Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 81661-31-6
• Molecular Formula: C₃₅H₄₆O₁₉
• Molecular Weight: 770.739

Synonyms:

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

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

There total 4 articles about Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-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: 27.0%

2,3-di-O-acetyl-4-O-benzyl-α,β-D-xylopyranosyl bromide (81703-86-8) + methyl-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (78423-96-8) → Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2S,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (78423-97-9) + Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (81661-31-6)

Guidance literature:

mercury(II) cyanide; In acetonitrile; for 1h;

DOI:10.1016/S0008-6215(00)81034-4

Reference yield:

methyl 2,3-di-O-acetyl-β-D-xylopyranoside (70003-50-8) → Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (81661-31-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 54.5 percent / mercuric cyanide / toluene; acetonitrile / 1 h

2: hydrogen / 5percent palladium-on-charcoal / 760 Torr

3: 27 percent / mercuric cyanide / acetonitrile / 1 h

With hydrogen; palladium on activated charcoal; mercury(II) cyanide; In toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)81034-4

Reference yield:

1,2,3-tri-O-acetyl-4-O-benzyl-β-D-xylopyranose (78423-89-9) → Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (81661-31-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide / CH₂Cl₂; toluene / 0.25 h / Ambient temperature

2: 27 percent / mercuric cyanide / acetonitrile / 1 h

With hydrogen bromide; mercury(II) cyanide; In dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)81034-4

upstream raw materials:

2,3-di-O-acetyl-4-O-benzyl-α,β-D-xylopyranosyl bromide

methyl-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

methyl 2,3-di-O-acetyl-β-D-xylopyranoside

1,2,3-tri-O-acetyl-4-O-benzyl-β-D-xylopyranose

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