Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 918800-26-7
• Molecular Formula: C₂₇H₂₉N₉O₉
• Molecular Weight: 623.582

Synonyms:Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 5 articles about Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 84.0%

Benzoic acid (2S,3R,4R,5S,6R)-3-azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (918800-29-0) + p-Anisaldehyde dimethyl acetal (2186-92-7) → Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (918800-26-7)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/j.bmcl.2006.09.013

Reference yield:

Paromamine (534-47-4,11030-86-7) → Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (918800-26-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / trifluoromethanesulfonyl azide; Et₃N; CuSO₄ / CH₂Cl₂; methanol; H₂O

2: 67 percent / camphor sulfonic acid / dimethylformamide / 110 °C

3: pyridine

4: trifluoroacetic acid / tetrahydrofuran; H₂O / 40 °C

5: 84 percent / camphor sulfonic acid / dimethylformamide / 50 °C

With pyridine; triflic azide; camphor-10-sulfonic acid; copper(II) sulfate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.09.013

Reference yield:

C24H35N9O7 (918800-25-6) → Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (918800-26-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: trifluoroacetic acid / tetrahydrofuran; H₂O / 40 °C

3: 84 percent / camphor sulfonic acid / dimethylformamide / 50 °C

With pyridine; camphor-10-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.09.013

upstream raw materials:

Benzoic acid (2S,3R,4R,5S,6R)-3-azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

p-Anisaldehyde dimethyl acetal

C₂₄H₃₅N₉O₇

Paromamine

Downstream raw materials:

(2R,3S,4R,5R,6S)-5-Amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5R)-5-aminomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

(2R,3S,4R,5R,6S)-5-Azido-6-[(1R,2S,3S,4R,6S)-4,6-diazido-3-((2S,3R,4S,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

C₃₈H₃₈N₁₂O₁₃

4-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-6-O-(β-ribofuranosyl)-2-desoxystreptamin

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