(2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol

Base Information

• Chemical Name: (2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol
• CAS No.: 866003-65-8
• Molecular Formula: C₂₆H₄₂O₇
• Molecular Weight: 466.615

Synonyms:(2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol

Chemical Property of (2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol

Chemical Property:

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Technology Process of (2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol

There total 2 articles about (2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-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: 87.0%

2,2-dimethyl-propanol-1 (75-84-3) + benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside (550346-02-6) → (2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol (866003-65-8)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 12h; Heating;

DOI:10.1021/jo050928f

Reference yield:

2,2,3,3-tetramethoxybutane (176798-33-7) → (2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol (866003-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / CH(OMe)3; (+/-)-CSA / 12 h / Heating

2: 87 percent / p-TsOH / benzene / 12 h / Heating

With 10-camphorsufonic acid; toluene-4-sulfonic acid; trimethyl orthoformate; In benzene;

DOI:10.1021/jo050928f

Reference yield: 96.0%

(2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol (866003-65-8) → (2R,3R,4aR,5S,8aR)-5-Benzyloxy-2,3-bis-(2,2-dimethyl-propoxy)-2,3-dimethyl-tetrahydro-pyrano[3,4-b][1,4]dioxin-8-one

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jo050928f

upstream raw materials:

2,2-dimethyl-propanol-1

benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside

2,2,3,3-tetramethoxybutane

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