(3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

Base Information

Chemical Name:(3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone
CAS No.:154815-48-2
Molecular Formula:C₂₁H₂₅NO₅
Molecular Weight:371.433
Hs Code.:

Synonyms:(3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

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Chemical Property of (3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

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Technology Process of (3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

There total 2 articles about (3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-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: 93.0%

: 154815-47-1
(3S,4R,5R)-3-benzoyloxy-1-benzyl-4-benzyloxy-5-methoxymethoxymethyl-2-pyrrolidinone

: 154815-48-2
(3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

Guidance literature:: With sodium hydroxide; In methanol; for 0.5h; Ambient temperature;
DOI:10.1248/cpb.41.1717

Reference yield:

: 127298-78-6
(3R,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-(methoxymethoxy)methyl-2-pyrrolidinone

: 154815-48-2
(3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

2: 93 percent / 2M aq. NaOH / methanol / 0.5 h / Ambient temperature

With sodium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;
DOI:10.1248/cpb.41.1717

Reference yield:

: 154815-48-2
(3S,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-methoxymethoxymethyl-2-pyrrolidinone

: (1R,2R,8S,8aR)-4-Benzyl-1,2,8-tris-benzyloxy-octahydro-indolizinium; chloride

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) THF, DMF, RT, 3 h

2: 82 percent / a) borane-dimethyl sulfide complex, b) 10percent aq. HCl / a) THF, 70 deg C, 1 h, b) THF, MeOH, 70 deg C, 1 h

3: DMSO, oxalyl chloride / CH₂Cl₂ / a) -20 deg C,

4: 30 percent / tetrahydrofuran / 1 h / -78 °C

5: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) THF, DMF, RT, 3 h

6: 1.) borane-THF complex, 2.) 3N aq. NaOH, 30percent H₂O₂ / 1.) THF, 40 deg C, 45 min, 2.) THF, 60 deg C, 30 min

7: methanesulfonyl chloride, Et₃N / CH₂Cl₂ / 14 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; borane-THF; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.41.1717