(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

Base Information

Chemical Name:(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran
CAS No.:223693-12-7
Molecular Formula:C₁₇H₂₃IO₂
Molecular Weight:386.273
Hs Code.:

Synonyms:(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

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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,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

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Technology Process of (2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

There total 6 articles about (2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran 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: 94.0%

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

: 223693-12-7
(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In benzene;
DOI:10.1021/ja990384x

Reference yield:

: 100-39-0
benzyl bromide

: 223693-12-7
(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

Guidance literature:: Multi-step reaction with 3 steps

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

2: 98 percent / TBAF / tetrahydrofuran / 1.5 h

3: 94 percent / PPh₃; imidazole; I₂ / benzene / 1.5 h

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; sodium hydride; triphenylphosphine; sodium iodide; In tetrahydrofuran; benzene; 1: benzylation / 2: desilylation / 3: Iodination;
DOI:10.1021/ja993487o

Reference yield:

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

: 223693-12-7
(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran

Guidance literature:: Multi-step reaction with 5 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

5: 94 percent / PPh₃; imidazole; I₂ / benzene / 1.5 h

With 1H-imidazole; triethylsilane; tetrabutyl ammonium fluoride; iodine; tin(IV) chloride; sodium hydride; triphenylphosphine; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 1: Substitution / 2: dehydroxylation / 3: benzylation / 4: desilylation / 5: Iodination;
DOI:10.1021/ja993487o