(2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol

Base Information

• Chemical Name: (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS No.: 105878-97-5
• Molecular Formula: C₁₃H₁₇NO₅
• Molecular Weight: 267.282
• Mol file: 105878-97-5.mol

Synonyms:(2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol

Chemical Property of (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol

There total 15 articles about (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 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%

1,4-dideoxy-1,4-imino-D-arabitol (100937-52-8,186759-56-8,187339-50-0) + benzyl chloroformate (501-53-1,94274-21-2) → (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol (105878-97-5)

Guidance literature:

With sodium hydroxide; for 1h; Ambient temperature;

DOI:10.1248/cpb.39.2807

Reference yield: 46.0%

dihydroxyacetone (96-26-4,26776-70-5) + N-benzyloxycarbonylglycinal (67561-03-9) → (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol (105878-97-5)

Guidance literature:

dihydroxyacetone; N-benzyloxycarbonylglycinal; With D-fructose-6-phosphate aldolase mutant A₁₆₅G; In N,N-dimethyl-formamide; at 25 ℃; for 24h; pH=7; Enzymatic reaction;

With palladium 10% on activated carbon; hydrogen; In ethanol; under 2585.81 Torr;

DOI:10.1039/c3ob27343a

Reference yield:

(2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol (108692-47-3) → (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol (105878-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂ / 10percent Pd-C / H₂O / 4 h / 3040 Torr / Ambient temperature

2: 88 percent / 1N aq. NaOH / 1 h / Ambient temperature

With sodium hydroxide; hydrogen; palladium on activated charcoal; In water;

DOI:10.1248/cpb.39.2807

upstream raw materials:

methyl N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-α-D-lyxofuranoside

(2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((phenylamino)methyl)pyrrolidine

1,4-dideoxy-1,4-imino-D-arabitol

benzyl chloroformate

Downstream raw materials:

N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-5-O-triphenylmethyl-D-arabinitol

(2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine hydrochloride

(2R,3R,4R)-3,4-dihydroxy-2-((phenylamino)methyl)pyrrolidine

(2R,3R,4R)-2-((benzylamino)methyl)-3,4-dihydroxypyrrolidine

Refernces

• 1、 -. "HIV protease inhibitors". Page/Page column 43; 44-45. . Retrieved 2010/02/11.
• 2、 Kayakiri, Hiroshi,Takase, Shigehiro,Setoi, Hiroyuki,Uchida, Itsuo,Terano, Hiroshi,Hashimoto, Masashi. "STRUCTURE OF FR 900483, A NEW IMMUNOMODULATOR ISOLATED FROM A FUNGUS". . p. 1725 - 1728. Retrieved 2007/10/02.