(2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 204510-88-3
• Molecular Formula: C₂₇H₂₇N₃O₅
• Molecular Weight: 473.528

Synonyms:(2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

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Technology Process of (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 5 articles about (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 90.0%

benzyl bromide (100-39-0) + 4,6-O-benzylidene-β-D-galactopyranosyl azide (204510-86-1) → (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (204510-88-3)

Guidance literature:

4,6-O-benzylidene-β-D-galactopyranosyl azide; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1039/c3cc47734g

Reference yield:

1-amido-1-deoxygalactopyranose (35899-89-9) → (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (204510-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / p-toluenesulfonic acid / acetonitrile

2: 86 percent / sodium hydride / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(03)00475-1

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (204510-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / p-toluenesulfonic acid / acetonitrile

2: 86 percent / sodium hydride / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(03)00475-1

upstream raw materials:

benzyl bromide

4,6-O-benzylidene-β-D-galactopyranosyl azide

1-amido-1-deoxygalactopyranose

benzaldehyde dimethyl acetal

Downstream raw materials:

1-(4',6'-O-benzylidene-2',3'-di-O-benzyl-β-D-galactosyl)-4-(p-tolyl)-1,2,3-triazole

Benzoic acid (2R,3S,4S,5R,6R)-6-azido-4,5-bis-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

2,3,6-tri-O-benzyl-β-D-galactopyranosyl azide

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