(2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol

Base Information

• Chemical Name: (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol
• CAS No.: 155885-28-2
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.416

Synonyms:(2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol

Chemical Property of (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol

Chemical Property:

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Technology Process of (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol

There total 2 articles about (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol 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: 76.0%

(2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester (155975-27-2) → (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol (155885-28-2)

Guidance literature:

With potassium hydroxide; In methanol; at 120 ℃;

DOI:10.1039/c39940000933

Reference yield:

(R)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester (155975-26-1) → (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol (155885-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NaBH(OAc)3, AcOH / CH₂Cl₂ / Ambient temperature

2: 76 percent / KOH / methanol / 120 °C

With potassium hydroxide; sodium tris(acetoxy)borohydride; acetic acid; In methanol; dichloromethane;

DOI:10.1039/c39940000933

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + (2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidin-3-ol (155885-28-2) → (3aS,9S,9aS)-9-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5,7,7-tetraisopropyl-hexahydro-4,6,8-trioxa-1-aza-5,7-disila-cyclopentacyclooctene

Guidance literature:

With pyridine;

DOI:10.1039/c39940000933

upstream raw materials:

(2S,3S)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester

(R)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3-oxo-pyrrolidine-1-carboxylic acid ethyl ester

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