(2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 868159-63-1
• Molecular Formula: C₂₈H₃₇NO₉
• Molecular Weight: 531.603
• Mol file: 868159-63-1.mol

Synonyms:

Chemical Property of (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

There total 8 articles about (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 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: 93.0%

(2R,3S,4S)-3,4-Bis-(2-methoxy-ethoxymethoxy)-2-trityloxymethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (868159-62-0) → (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (868159-63-1)

Guidance literature:

With formic acid; In acetonitrile; at 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2005.07.072

Reference yield:

(3R,4S,5S)-3,4-Bis-(2-methoxy-ethoxymethoxy)-5-trityloxymethyl-dihydro-furan-2-one (868159-58-4) → (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (868159-63-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / LiBH₄ / tetrahydrofuran / 2.5 h / 20 °C

2: 90 percent / DMAP; pyridine / 5 h / 20 °C

3: 99 percent / 96 h / 90 °C

4: H₂ / Pd/C / ethanol / 16 h

5: 2.56 g / triethylamine / toluene / 2 h / 20 °C

6: 93 percent / formic acid / acetonitrile / 2.5 h / 20 °C

With pyridine; dmap; lithium borohydride; formic acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene; acetonitrile;

DOI:10.1016/j.tet.2005.07.072

Reference yield:

(2S,3S,4S)-2,3-Bis-(2-methoxy-ethoxymethoxy)-5-trityloxy-pentane-1,4-diol (868159-59-5) → (2R,3S,4S)-2-Hydroxymethyl-3,4-bis-(2-methoxy-ethoxymethoxy)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (868159-63-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / DMAP; pyridine / 5 h / 20 °C

2: 99 percent / 96 h / 90 °C

3: H₂ / Pd/C / ethanol / 16 h

4: 2.56 g / triethylamine / toluene / 2 h / 20 °C

5: 93 percent / formic acid / acetonitrile / 2.5 h / 20 °C

With pyridine; dmap; formic acid; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; toluene; acetonitrile;

DOI:10.1016/j.tet.2005.07.072

upstream raw materials:

(2R,3S,4S)-3,4-Bis-(2-methoxy-ethoxymethoxy)-2-trityloxymethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

(3R,4S,5S)-3,4-Bis-(2-methoxy-ethoxymethoxy)-5-trityloxymethyl-dihydro-furan-2-one

(2S,3S,4S)-2,3-Bis-(2-methoxy-ethoxymethoxy)-5-trityloxy-pentane-1,4-diol

(2R,3S,4S)-1-Benzyl-3,4-bis-(2-methoxy-ethoxymethoxy)-2-trityloxymethyl-pyrrolidine