(3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone

Base Information

• Chemical Name: (3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone
• CAS No.: 124665-84-5
• Molecular Formula: C₃₂H₃₅NO₆
• Molecular Weight: 529.633
• Mol file: 124665-84-5.mol

Synonyms:(3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone

Chemical Property of (3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone

There total 8 articles about (3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-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: 88.0%

(3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-5-trityloxymethyl-2-pyrrolidinone (124665-83-4) + 2,2-dimethoxy-propane (77-76-9) → (3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone (124665-84-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 2h; Ambient temperature;

Reference yield:

(S)-2-Oxo-5-trityloxymethyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (124665-82-3) → (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone (124665-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O

2: p-TsOH / acetone

With osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In water; acetone;

DOI:10.1016/S0040-4039(00)92240-8

Reference yield:

(3R,4R,5R)-3,4-Dihydroxy-2-oxo-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (127298-73-1) + 2,2-dimethoxy-propane (77-76-9) → (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone (124665-84-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetone;

DOI:10.1016/S0040-4039(00)92240-8

upstream raw materials:

(3R,4R,5R)-3,4-Dihydroxy-2-oxo-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

2,2-dimethoxy-propane

(S)-2-Oxo-5-trityloxymethyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

(3S,4S,5S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-5-trityloxymethyl-2-pyrrolidinone

Downstream raw materials:

(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

(2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-vinylpyrrolidine

{(R)-1-[(4R,5S)-5-(1-Hydroxy-allyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-trityloxy-ethyl}-carbamic acid tert-butyl ester

tert-butyl (3aS,4R,6R,6aR)-4-{{[(tert-butyl)dimethylsilyl]oxy}methyl}tetrahydro-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate