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

Base Information

• Chemical Name: (2S,4aR,6S,7S,8S,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 149553-15-1
• Molecular Formula: C₂₂H₂₆O₇
• Molecular Weight: 402.444

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

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

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

There total 1 articles about (2S,4aR,6S,7S,8S,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:

Benzyloxymethyl chloride (3587-60-8) + methyl 4,6-O-(S)-benzylidene-α-D-idopyranoside (74560-56-8) → (2S,4aR,6S,7S,8S,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (149553-15-1) + (2S,4aR,6S,7S,8R,8aR)-7-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (149553-14-0) + (2S,4aR,6S,7S,8R,8aS)-7,8-Bis-benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, 2.)a) THF, hexane, 0 deg C, 2 h, b) RT, 5 h;

DOI:10.1248/cpb.41.491

Reference yield: 82.0%

(2S,4aR,6S,7S,8S,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (149553-15-1) → (2S,4aR,6S,8R,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (149553-18-4)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; at 50 ℃; for 3h;

DOI:10.1248/cpb.41.491

upstream raw materials:

Benzyloxymethyl chloride

methyl 4,6-O-(S)-benzylidene-α-D-idopyranoside

Downstream raw materials:

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

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