(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran
CAS No.:552849-97-5
Molecular Formula:C₂₁H₃₂O₆
Molecular Weight:380.481
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

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Chemical Property of (2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

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Technology Process of (2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

There total 13 articles about (2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran 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:

: 1-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol

: 552849-97-5
(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Guidance literature:: With 2,6-dimethylpyridine; Dess-Martin periodane; In dichloromethane;
DOI:10.1002/anie.200390321

Reference yield:

: 201854-68-4
1-[6-allyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydropyran-2-yl]-ethane-1,2-diol

: 552849-97-5
(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Guidance literature:: Multi-step reaction with 7 steps

1: N-tosylimidazole; NaH / diethyl ether / -78 - 0 °C

2: LiAlH₄ / diethyl ether

3: 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

4: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O

5: NaIO₄ on silica / CH₂Cl₂

6: camphorsulfonic acid / CH₂Cl₂

7: Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; N-tosylimidazole; In diethyl ether; dichloromethane; water; acetone; 7: Dess-Martin oxidation;
DOI:10.1002/anie.200390321

Reference yield:

: 1-[(2R,3R,4S,5S,6R)-6-Allyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

: 552849-97-5
(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

1: LiAlH₄ / diethyl ether

2: 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

3: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O

4: NaIO₄ on silica / CH₂Cl₂

5: camphorsulfonic acid / CH₂Cl₂

6: Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; Dess-Martin periodane; 4-methylmorpholine N-oxide; In diethyl ether; dichloromethane; water; acetone; 6: Dess-Martin oxidation;
DOI:10.1002/anie.200390321