(2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

Base Information

Chemical Name:(2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran
CAS No.:223692-98-6
Molecular Formula:C₂₄H₃₀O₄S
Molecular Weight:414.566
Hs Code.:

Synonyms:(2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

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Chemical Property of (2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

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Technology Process of (2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

There total 8 articles about (2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-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: 69.0%

: 3112-85-4
methylphenylsulfonate

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

: 223692-98-6
(2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

Guidance literature:: methylphenylsulfonate; With n-butyllithium; In hexane; at -78 ℃; for 0.416667h;

(2S,3R,4S,6R)-6-allyl-4-(benzyloxy)-6-iodomethyltetrahydro-3-methyl-2H-pyran; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 8h; Further stages.;
DOI:10.1021/ja993487o

Reference yield: 69.0%

: 116511-95-6
(benzenesulfonyl)methyllithium

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

: 223692-98-6
(2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/ja990384x

Reference yield:

: 100-39-0
benzyl bromide

: 223692-98-6
(2S,3R,4S,6S)-2-allyl-4-(benzyloxy)tetrahydro-3-methyl-6-[2-(phenylsulfonyl)ethyl]-2H-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / NaH; NaI / tetrahydrofuran / 0.33 h / Heating

2.1: 98 percent / TBAF / tetrahydrofuran / 1.5 h

3.1: 94 percent / PPh₃; imidazole; I₂ / benzene / 1.5 h

4.1: n-BuLi / hexane / 0.42 h / -78 °C

4.2: 69 percent / HMPA / hexane; tetrahydrofuran / 8 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; iodine; sodium hydride; triphenylphosphine; sodium iodide; In tetrahydrofuran; hexane; benzene; 1.1: benzylation / 2.1: desilylation / 3.1: Iodination / 4.1: Metallation / 4.2: Condensation;
DOI:10.1021/ja993487o