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

Base Information

• Chemical Name: (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine
• CAS No.: 212892-52-9
• Molecular Formula: C₃₃H₃₉NO₆
• Molecular Weight: 545.676
• Mol file: 212892-52-9.mol

Synonyms:(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

Chemical Property of (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

There total 9 articles about (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine 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: 82.0%

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 (212892-12-1) → (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine (212892-52-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00542-0

Reference yield:

(3aS,6R,6aR)-4-Formyl-2,2-dimethyl-6-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester → (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine (212892-52-9) + (2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine (212892-50-7)

Guidance literature:

With sodium tetrahydroborate; In diethyl ether; ethanol; at 0 ℃;

DOI:10.1016/S0040-4020(98)00542-0

Reference yield:

[(R)-1-((4R,5R)-5-Acryloyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester (126199-70-0) → (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine (212892-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / NaBH₄ / methanol / 0 - 20 °C

2: 68 percent / MsCl, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

4: 146 mg / NaBH₄ / ethanol; CH₂Cl₂ / 0 °C

With sodium tetrahydroborate; ozone; methanesulfonyl chloride; triethylamine; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)00542-0

upstream raw materials:

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

[(R)-1-((4R,5R)-5-Acryloyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

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

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

Downstream raw materials:

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

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

tert-butyl (3aR,4R,6R,6aS)-4-[(benzylamino)methyl]tetrahydro-6-[(methoxymethoxy)methyl]-2,2-dimethyl-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

(2R,3R,4S,5R)-N-benzyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-methoxymethyloxy-3-hydroxypropanyl)pyrrolidine