(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

Base Information

Chemical Name:(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol
CAS No.:223692-97-5
Molecular Formula:C₁₇H₂₄O₃
Molecular Weight:276.376
Hs Code.:

Synonyms:(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

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Technology Process of (2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

There total 5 articles about (2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol 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: 98.0%

: 261374-46-3
[[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]methoxy]-tert-butyldiphenylsilane

: 223692-97-5
(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ja990384x

Reference yield:

: 100-39-0
benzyl bromide

: 223692-97-5
(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / NaH; NaI / tetrahydrofuran / 0.33 h / Heating

2: 98 percent / TBAF / tetrahydrofuran / 1.5 h

With tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran; 1: benzylation / 2: desilylation;
DOI:10.1021/ja993487o

Reference yield:

: (3R,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one

: 223692-97-5
(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: tetrahydrofuran; diethyl ether / 0.08 h / -78 °C

2: 71 percent / Et₃SiH; SnCl₄ / CH₂Cl₂ / 1.33 h / -78 - -20 °C

3: 87 percent / NaH; NaI / tetrahydrofuran / 0.33 h / Heating

4: 98 percent / TBAF / tetrahydrofuran / 1.5 h

With triethylsilane; tetrabutyl ammonium fluoride; tin(IV) chloride; sodium hydride; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Substitution / 2: dehydroxylation / 3: benzylation / 4: desilylation;
DOI:10.1021/ja993487o