(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

Base Information

Chemical Name:(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane
CAS No.:906624-08-6
Molecular Formula:C₁₈H₂₅IO₃
Molecular Weight:416.299
Hs Code.:

Synonyms:(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

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Chemical Property of (2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

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Technology Process of (2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

There total 3 articles about (2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane 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: 79.0%

: C₁₈H₂₆O₄

: 906624-08-6
(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere; Darkness;
DOI:10.1021/jo802249k

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 906624-08-6
(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0 °C

2.1: aq. TBHP; salicylic acid; SeO₂ / CH₂Cl₂

2.2: NaBH₄ / methanol

3.1: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 0 °C

4.1: I₂; PPh₃; imidazole / diethyl ether; acetonitrile / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; selenium(IV) oxide; diethyl (2R,3R)-tartrate; iodine; sodium hydride; triphenylphosphine; salicylic acid; 4 A molecular sieve; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ja073952e

Reference yield:

: 698379-54-3
(2E,6E)-8-(4-Methoxy-benzyloxy)-2,6-dimethyl-octa-2,6-dien-1-ol

: 906624-08-6
(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

Guidance literature:: Multi-step reaction with 2 steps

1: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 0 °C

2: I₂; PPh₃; imidazole / diethyl ether; acetonitrile / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; iodine; triphenylphosphine; 4 A molecular sieve; In diethyl ether; dichloromethane; acetonitrile; 1: Sharpless asymmetric epoxidation;
DOI:10.1021/ja073952e