Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 204199-45-1
• Molecular Formula: C₄₂H₄₂ClN₃O₁₁S
• Molecular Weight: 832.328

Synonyms:Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

There total 5 articles about Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-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:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl chloride (67817-16-7) → Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (204199-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / 2,6-di-tert-butyl-4-methylpyridine, CF₃SO₂OAg / CH₂Cl₂ / 2 h / 0 °C

2: 79 percent / HBF₄*Et₂O / methanol / 72 h / 23 °C

3: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

4: pyridine / 0.17 h / 0 °C

With pyridine; tetrafluoroboric acid diethyl ether; 2,6-di-tert-butyl-4-methylpyridine; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

Reference yield:

phenyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-42-8) → Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (204199-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / 2,6-di-tert-butyl-4-methylpyridine, CF₃SO₂OAg / CH₂Cl₂ / 2 h / 0 °C

2: 79 percent / HBF₄*Et₂O / methanol / 72 h / 23 °C

3: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

4: pyridine / 0.17 h / 0 °C

With pyridine; tetrafluoroboric acid diethyl ether; 2,6-di-tert-butyl-4-methylpyridine; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

Reference yield:

phenyl (2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-44-0) → Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,4aR,6R,7R,8R,8aS)-7-azido-8-(2-chloro-acetoxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (204199-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

2: pyridine / 0.17 h / 0 °C

With pyridine; (1S)-10-camphorsulfonic acid; In dichloromethane;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

upstream raw materials:

Chloroacetic anhydride

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl chloride

phenyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl (2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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