(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

Base Information

Chemical Name:(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone
CAS No.:321887-33-6
Molecular Formula:C₂₇H₂₇NO₃
Molecular Weight:413.516
Hs Code.:

Synonyms:(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

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Chemical Property of (3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

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Technology Process of (3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

There total 6 articles about (3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone 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: 77.0%

: 321887-30-3
(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-1-(4-methoxyphenyl)-5-[(Z)-2-phenylethenyl]-2-pyrrolidinone

: 321887-33-6
(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 1h;
DOI:10.1021/jo0012187

Reference yield:

: 100-39-0
benzyl bromide

: 321887-33-6
(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h

1.2: 86 percent / 1 h / 20 °C

2.1: 85 percent / H₂ / Lindlar catalyst / benzene / 0.67 h / 2068.65 Torr

3.1: 77 percent / CAN / acetonitrile / 1 h / 0 °C

With ammonium cerium(IV) nitrate; hydrogen; sodium hydride; Lindlar's catalyst; In N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo0012187

Reference yield:

: 106318-93-8
phenylpropargylidene p-anisidine

: 321887-33-6
(3S,4S,5R)-3-benzyloxy-4-benzyloxymethyl-5-(2-phenylethenyl)-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2: 79 percent / P(o-tolyl)3; Et₃N / Pd(OAc)2 / 85 °C

3: 82 percent / H₂ / Pd black / ethanol / 2068.65 Torr

4: 77 percent / KHMDS; (2,4,5-triisopropyl)phenylsulfonyl azide / tetrahydrofuran; toluene / -78 °C

With n-butyllithium; 2,4,5-triisopropyl benzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; palladium; In tetrahydrofuran; ethanol; hexane; toluene; 1: Alkylation / 2: Heck coupling / 3: Hydrogenation / 4: Substitution;
DOI:10.1021/jo000643x