(4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

Base Information

• Chemical Name: (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde
• CAS No.: 200186-28-3
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:(4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

Chemical Property of (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

Chemical Property:

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Technology Process of (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

There total 5 articles about (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde 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%

C18H26O5 (1187556-13-3) → (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde (200186-28-3)

Guidance literature:

C₁₈H₂₆O₅; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.75h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.001

Reference yield: 92.0%

((4aR,7S,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-methanol → (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde (200186-28-3)

Guidance literature:

Swern oxidation;

DOI:10.1016/S0040-4039(97)10499-3

Reference yield:

(2R,3S,4R,5S)-4-Benzyloxy-2,6-bis-hydroxymethyl-5-methyl-tetrahydro-pyran-3-ol → (4aR,6R,7R,8R,8aS)-8-Benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde (200186-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / TsOH / benzene / Heating

2: 92 percent / Swern oxidation

With toluene-4-sulfonic acid; In benzene;

DOI:10.1016/S0040-4039(97)10499-3

upstream raw materials:

Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

C₁₈H₂₆O₅

Downstream raw materials:

(2S,3S,4R)-8-Benzyloxy-1-{2-[(S)-((2R,3R,4R,5S,6R)-4-benzyloxy-5-hydroxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-[1,3]dithian-2-yl}-3-methyl-octane-2,4-diol

2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-4-benzyloxy-6-[(S)-[(2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-methyl]-3-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

[(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-((4aR,6R,7R,8R,8aS)-8-benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-methoxy]-tert-butyl-dimethyl-silane

C₄₉H₉₂O₁₀Si₃

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