(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

Base Information

Chemical Name:(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol
CAS No.:342600-30-0
Molecular Formula:C₂₄H₂₈INO₄
Molecular Weight:521.395
Hs Code.:

Synonyms:(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

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Chemical Property of (2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

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Technology Process of (2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

There total 5 articles about (2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol 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:

: 342600-29-7
(3aS,9bS)-1-[(2S)-2-benzylpent-4-enoyl]-2,2-dimethyl-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

: 342600-30-0
(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

Guidance literature:: With N-iodo-succinimide; water; sodium hydrogencarbonate; In ethyl acetate; at 0 - 20 ℃; for 24h;

Reference yield:

: 106-95-6
allyl bromide

: 342600-27-5
(3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

: 342600-30-0
(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

Guidance literature:: allyl bromide; (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole; With lithium hexamethyldisilazane; In tetrahydrofuran; at -45 ℃; for 2h;

With N-chloro-succinimide; sodium hydrogencarbonate; sodium iodide; In Isopropyl acetate; water; at 5 - 30 ℃;
DOI:10.1016/j.tetasy.2003.09.023

Reference yield:

: 645-45-4
hydrocinnamic acid chloride

: 342600-30-0
(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 20 - 45 °C

2.1: 180 g / methanesulfonic acid / tetrahydrofuran / 35 - 60 °C

3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -45 °C

3.2: 64.0 g / N-chlorosuccinimide; NaHCO₃; NaI / H₂O; isopropyl acetate / 5 - 30 °C

With methanesulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/j.tetasy.2003.09.023