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

Base Information

• Chemical Name: (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 312308-11-5
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321

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

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

Chemical Property:

Purity/Quality:

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

There total 2 articles about (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-6-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: 100.0%

(2R,4S,5R)-4-((2R,3R)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol (1053720-31-2) → (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (312308-11-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;

DOI:10.1021/ol016355k

Reference yield:

{(2R,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxiranyl}-methanol (131310-57-1) → (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (312308-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / TBAF / tetrahydrofuran / 20 °C

2: 100 percent / PPTS / CH₂Cl₂ / 20 °C

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016355k

Reference yield: 100.0%

trifluoromethylsulfonic anhydride (358-23-6) + (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (312308-11-5) → Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8aS)-7-hydroxy-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl ester

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 78 ℃;

DOI:10.1021/ol016355k

upstream raw materials:

(2R,4S,5R)-4-((2R,3R)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

{(2R,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxiranyl}-methanol

Downstream raw materials:

(4aS,7R,8aS,9aR,10aR)-2,2,4a-Trimethyl-7-phenyl-hexahydro-1,3,6,8,10-pentaoxa-anthracene

[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde

((2R,4aR,6R,7S,8aR,9aS,10aS)-6-Hydroxy-6,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-acetic acid ethyl ester

C₂₉H₃₂O₅

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