Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 182812-51-7
• Molecular Formula: C₃₆H₄₂N₂O₁₇S
• Molecular Weight: 806.799

Synonyms:Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl 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: 98.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + Allyl O-(2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (182812-45-9) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester (182812-51-7)

Guidance literature:

In tetrahydrofuran; 1,2-dichloro-ethane; for 3h; Heating;

DOI:10.1080/07328309608005691

Reference yield:

benzoyl cyanide (613-90-1) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester (182812-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N / acetonitrile / 0.5 h / 0 °C

2: 98 percent / tetrahydrofuran; 1,2-dichloro-ethane / 3 h / Heating

With triethylamine; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1080/07328309608005691

Reference yield:

allyl O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (152733-62-5) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester (182812-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N / acetonitrile / 0.5 h / 0 °C

2: 98 percent / tetrahydrofuran; 1,2-dichloro-ethane / 3 h / Heating

With triethylamine; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1080/07328309608005691

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

Allyl O-(2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

benzoyl cyanide

allyl O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

Allyl O-(2,3-di-O-acetyl-6-O-benzoyl-4-deoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Benzoic acid (2S,4S,5R,6R)-4,5-diacetoxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

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