5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

Base Information

• Chemical Name: 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine
• CAS No.: 162992-53-2
• Molecular Formula: C₂₇H₃₁NO₄
• Molecular Weight: 433.547
• Mol file: 162992-53-2.mol

Synonyms:5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

Chemical Property of 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

There total 8 articles about 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine 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: 100.0%

(2S,3R,4R,5R)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine (881185-99-5) → 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine (162992-53-2)

Guidance literature:

With magnesium; In methanol; for 1h; Heating;

DOI:10.1016/j.tet.2005.11.037

Reference yield: 90.0%

8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one (162992-52-1) → 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine (162992-53-2)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 100 ℃; for 24h;

DOI:10.1021/jo00111a007

Reference yield:

2,5-anhydro-2,5-imino-D-glucitol (132295-44-4) → 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine (162992-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 10percent aq. NaHCO₃ / toluene / 1 h

2: 88 percent / NaH, KI / dimethylformamide / 12 h / Ambient temperature

3: 90 percent / aq. KOH / ethane-1,2-diol / 24 h / 100 °C

With potassium hydroxide; sodium hydride; sodium hydrogencarbonate; potassium iodide; In ethylene glycol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00111a007

upstream raw materials:

8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

(2S,3R,4R,5R)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine

3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

Acetic acid (2S,3R,4S)-3,4-bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Downstream raw materials:

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)-N-methylpyrrolidine

N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

2,5-anhydro-2,5-imino-D-glucitol

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-formyl-N-methylpyrrolidine