methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

Base Information

Chemical Name:methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate
CAS No.:317357-78-1
Molecular Formula:C₂₄H₂₇NO₇
Molecular Weight:441.481
Hs Code.:

Synonyms:methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

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Chemical Property of methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

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Technology Process of methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

There total 2 articles about methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate 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: 83.0%

: 111265-96-4
(2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 317357-78-1
methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 14h; Heating;
DOI:10.1248/cpb.54.1515

Reference yield:

: 191851-84-0
(2S,3R,4S)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-2-pyrrolidinylcarboxylic acid

: 317357-78-1
methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: BH₃*Me₂S / tetrahydrofuran / 1 h / Heating

2: 83 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 14 h / Heating

With di-isopropyl azodicarboxylate; dimethylsulfide borane complex; triphenylphosphine; In tetrahydrofuran; 2: Mitsunobu reaction;
DOI:10.1248/cpb.54.1515

Reference yield:

: 317357-78-1
methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate

: 317357-81-6
methyl 4-[(3R,4S)-dihydroxy-1-[4-[N-(2-methylphenyl)ureido]-3-methoxyphenylacetyl]-(2R)-pyrrolidinyl]methoxybenzoate

Guidance literature:: Multi-step reaction with 3 steps

1: 53 percent / H₂ / Pd/C / ethanol / 144 h / 20 °C

2: 100 percent / EDC*HCl; HOBt; DMAP / dimethylformamide / 12 h / 20 °C

3: 95 percent / HCl(gas) / methanol / 17 h / 20 °C

With hydrogenchloride; dmap; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.54.1515