(2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

• Chemical Name: (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 149553-06-0
• Molecular Formula: C₂₂H₂₆O₇
• Molecular Weight: 402.444

Synonyms:(2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property of (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property:

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Technology Process of (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 3 articles about (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 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: 92.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl 3-O-benzyloxymethyl-α-D-galactopyranoside (149553-05-9) → (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (149553-06-0)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 2h;

DOI:10.1248/cpb.41.491

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (149553-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) dioxane, 80 deg C, 2 h

2: 92 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.41.491

Reference yield:

methyl α-D-galactopyranoside (3396-99-4) → (2S,4aR,6S,7R,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (149553-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) dioxane, 80 deg C, 2 h

2: 92 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.41.491

upstream raw materials:

benzaldehyde dimethyl acetal

methyl 3-O-benzyloxymethyl-α-D-galactopyranoside

Benzyloxymethyl chloride

methyl α-D-galactopyranoside

Downstream raw materials:

(2S,4aR,6S,8S,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

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