tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate

Base Information

• Chemical Name: tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate
• CAS No.: 359849-10-8
• Molecular Formula: C₁₈H₂₄O₅Se
• Molecular Weight: 399.346

Synonyms:tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate

Chemical Property of tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate

Chemical Property:

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Technology Process of tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate

There total 2 articles about tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate 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: 50.0%

Phenylselenyl bromide (34837-55-3) + tert-butyl (4S)-5-tert-butoxycarbonyloxy-2,4-dimethylpent-2-enoate (359849-09-5) → tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate (359849-10-8)

Guidance literature:

With silver trifluoromethanesulfonate; sodium hydrogencarbonate; In acetonitrile; at 20 ℃;

DOI:10.1021/jo010310f

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate (359849-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / tetrahydrofuran / 2 h / 20 °C

2: 50 percent / NaHCO₃; AgOTf / acetonitrile / 20 °C

With dmap; silver trifluoromethanesulfonate; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo010310f

Reference yield: 50.0%

tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate (359849-10-8) → tert-butyl (2R,3R,4R)-3,5-dihydroxy-2-phenylseleno-2,4-dimethylpentanoate (359849-13-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1021/jo010310f

upstream raw materials:

Phenylselenyl bromide

tert-butyl (4S)-5-tert-butoxycarbonyloxy-2,4-dimethylpent-2-enoate

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (2R,3R,4R)-3,5-dihydroxy-2-phenylseleno-2,4-dimethylpentanoate

(2S,3R)-3-benzyloxymethoxy-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentane

(2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol

(3R,4R,5S,6R)-6-[(1R)-2-(tert-butyldiphenylsilyloxy-1-methylethyl)]-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

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