3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(2-thienyl)-, [2R-(2alpha,3ba,4ba,5alpha)]- (9CI)

Base Information

• Chemical Name: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(2-thienyl)-, [2R-(2alpha,3ba,4ba,5alpha)]- (9CI)
• CAS No.: 180895-71-0
• Molecular Formula: C₉H₁₃NO₃S
• Molecular Weight: 215.273
• Mol file: 180895-71-0.mol

Synonyms:3,4-Pyrrolidinediol,2-(hydroxymethyl)-5-(2-thienyl)-,[2R-(2alpha,3bta,4bta,5alpha)]-(9CI);3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(2-thienyl)-, [2R-(2alpha,3ba,4ba,5alpha)]- (9CI)

Chemical Property of 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(2-thienyl)-, [2R-(2alpha,3ba,4ba,5alpha)]- (9CI)

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(2-thienyl)-, [2R-(2alpha,3ba,4ba,5alpha)]- (9CI)

There total 3 articles about 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(2-thienyl)-, [2R-(2alpha,3ba,4ba,5alpha)]- (9CI) 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: 94.0%

5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-(2-thienyl)-β-D-ribitol → 1,4-Dideoxy-1,4-imino-1β-(2'-thienyl)-D-ribitol (180895-71-0,747398-65-8)

Guidance literature:

With water; trifluoroacetic acid; at 50 ℃; for 2h;

DOI:10.1021/jo960523i

Reference yield:

(3S,4R)-1-O-tert-butyldimethylsilyl-1,3,4-trihydroxy-3,4-O-isopropylidene-1-(thiophen-2-yl)-2,5-pentanedione (180895-65-2) → 1,4-Dideoxy-1,4-imino-1β-(2'-thienyl)-D-ribitol (180895-71-0,747398-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / ammonium formate; NaBH₃CN; molecular sieves (3A) / methanol / 18 h / 20 °C

2: 94 percent / trifluoroacetic acid; water / 2 h / 50 °C

With 3 A molecular sieve; water; ammonium formate; sodium cyanoborohydride; trifluoroacetic acid; In methanol; 1: Cyclization / 2: Hydrolysis;

DOI:10.1021/jo960523i

Reference yield:

2-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-α,β-D-ribopentitol-1-yl)thiophene (196106-54-4) → 1,4-Dideoxy-1,4-imino-1β-(2'-thienyl)-D-ribitol (180895-71-0,747398-65-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 2 h / -78 °C

1.2: 80 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

2.1: 34 percent / ammonium formate; NaBH₃CN; molecular sieves (3A) / methanol / 18 h / 20 °C

3.1: 94 percent / trifluoroacetic acid; water / 2 h / 50 °C

With 3 A molecular sieve; water; ammonium formate; sodium cyanoborohydride; dimethyl sulfoxide; trifluoroacetic acid; trifluoroacetic anhydride; In methanol; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Cyclization / 3.1: Hydrolysis;

DOI:10.1021/jo960523i

upstream raw materials:

(3S,4R)-1-O-tert-butyldimethylsilyl-1,3,4-trihydroxy-3,4-O-isopropylidene-1-(thiophen-2-yl)-2,5-pentanedione

2-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-α,β-D-ribopentitol-1-yl)thiophene

Refernces