Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 182865-72-1
• Molecular Formula: C₃₃H₄₃NO₁₆
• Molecular Weight: 709.702

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose (112929-24-5,112929-25-6) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester (182865-72-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / TMSOTf, MS₄A / 1,2-dichloro-ethane

2: 98 percent / NaOMe / methanol

3: 100 percent / p-TosOH / acetonitrile

4: 61 percent / Hg(CN)2, HgBr₂, MS₄A / 1,2-dichloro-ethane

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; mercury dibromide; In methanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/0960-894X(96)00370-8

Reference yield:

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester (182865-98-1) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester (182865-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / p-TosOH / acetonitrile

2: 61 percent / Hg(CN)2, HgBr₂, MS₄A / 1,2-dichloro-ethane

With mercury(II) cyanide; toluene-4-sulfonic acid; mercury dibromide; In 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/0960-894X(96)00370-8

Reference yield: 73.0%

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-allyloxycarbonylamino-6-ethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester (182865-72-1) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6R)-3-allyloxycarbonylamino-6-benzyloxymethyl-2-ethoxy-5-hydroxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester (182865-74-3)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In tetrahydrofuran; 0 deg C -> room temperature;

DOI:10.1016/0960-894X(96)00370-8

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6R)-3-allyloxycarbonylamino-6-benzyloxymethyl-2-ethoxy-5-hydroxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-amino-2-benzyloxymethyl-6-ethoxy-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-amino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

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