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

Base Information

• Chemical Name: Benzoic acid (2R,4aR,6S,7R,8S,8aS)-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester
• CAS No.: 471891-14-2
• Molecular Formula: C₂₇H₂₅N₃O₆
• Molecular Weight: 487.512

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 7 articles about Benzoic acid (2R,4aR,6S,7R,8S,8aS)-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-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: 81.0%

benzyl bromide (100-39-0) + 2-azido-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl benzoate (471891-13-1) → Benzoic acid (2R,4aR,6S,7R,8S,8aS)-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester (471891-14-2)

Guidance literature:

With silver(l) oxide;

DOI:10.1016/S0040-4039(02)00919-X

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Benzoic acid (2R,4aR,6S,7R,8S,8aS)-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester (471891-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TfN₃; CuSO₄; CSA

1.2: 75 percent / CSA

2.1: Et₃N

3.1: 74 percent / NaNO₂; 15-crown-5; HMPA

4.1: 81 percent / Ag₂O

With N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; triflic azide; camphor-10-sulfonic acid; copper(II) sulfate; triethylamine; silver(l) oxide; sodium nitrite;

DOI:10.1016/S0040-4039(02)00919-X

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → Benzoic acid (2R,4aR,6S,7R,8S,8aS)-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester (471891-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TfN₃; CuSO₄; CSA

1.2: 75 percent / CSA

2.1: Et₃N

3.1: 74 percent / NaNO₂; 15-crown-5; HMPA

4.1: 81 percent / Ag₂O

With N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; triflic azide; camphor-10-sulfonic acid; copper(II) sulfate; triethylamine; silver(l) oxide; sodium nitrite;

DOI:10.1016/S0040-4039(02)00919-X

upstream raw materials:

benzyl bromide

2-azido-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl benzoate

benzaldehyde dimethyl acetal

N-benzoyloxybenzotriazole

Downstream raw materials:

2-azido-3,4-di-O-benzyl-2-deoxy-β-D-allopyranosyl benzoate

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