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

Base Information

• Chemical Name: (4aR,6S,7R,8aS)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 62222-26-8
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321

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

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

Chemical Property:

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

There total 4 articles about (4aR,6S,7R,8aS)-6-Methoxy-7-methyl-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: 73.0%

methyl magnesium iodide (917-64-6) + Methyl-4,6-O-benzyliden-3-deoxy-α-D-erythro-hexo-pyranosid-2-ulose (19272-50-5) → (4aR,6S,7R,8aS)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (62222-26-8)

Guidance literature:

In diethyl ether; at -65 ℃; for 4h;

DOI:10.1021/jo00345a007

Reference yield: 49.0%

(1aS,2S,6R,7bS)-2-Methoxy-1a-methyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene (95058-48-3,95058-50-7,101978-76-1,101978-77-2) → (2R,6S,7S)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (62222-26-8,62222-27-9)

Guidance literature:

With lithium aluminium tetrahydride; In 1,4-dioxane; for 8h; Heating;

DOI:10.1016/0008-6215(86)85034-0

Reference yield: 48.0%

(1aR,2S,6R,7bR)-2-Methoxy-1a-methyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene (95058-48-3,95058-50-7,101978-76-1,101978-77-2) → (2R,6S,7R)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (62222-26-8,62222-27-9) + (2R,6S,7R,8S)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (19465-06-6,68907-47-1,75879-81-1,75879-82-2,75879-83-3,101978-79-4,130061-59-5)

Guidance literature:

With lithium aluminium tetrahydride; In 1,4-dioxane; for 8h; Heating;

DOI:10.1016/0008-6215(86)85034-0

upstream raw materials:

methyl magnesium iodide

Methyl-4,6-O-benzyliden-3-deoxy-α-D-erythro-hexo-pyranosid-2-ulose

methyllithium

(1aR,2S,6R,7bR)-2-Methoxy-1a-methyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene

Downstream raw materials:

methyl 2-O-benzyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-ribo-hexopyranoside

methyl 2-O-benzyl-2-C-methyl-α-D-ribo-hexopyranoside

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