(3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose

Base Information

• Chemical Name: (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose
• CAS No.: 121742-13-0
• Molecular Formula: C₁₃H₁₇NO₆
• Molecular Weight: 283.281
• Mol file: 121742-13-0.mol

Synonyms:(3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose

Chemical Property of (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose

There total 5 articles about (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose 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: 89.0%

C13H19NO6 → (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose (121742-13-0)

Guidance literature:

With G_. oxydans DSM 2003 cells; In water; at 35 ℃; for 16h; pH=6.8; Temperature; Concentration; regioselective reaction; Microbiological reaction;

DOI:10.1039/d1cy00698c

Reference yield: 82.0%

dihydroxyacetone (96-26-4,26776-70-5) + N-benzyloxycarbonylglycinal (67561-03-9) → (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose (121742-13-0)

Guidance literature:

With double mutant D-fructose-6-phosphate aldolase A₁₂₉S/A₁₆₅G; In N,N-dimethyl-formamide; at 25 ℃; for 24h; pH=7.5; aq. buffer; Enzymatic reaction;

DOI:10.1039/c1cc11069a

Reference yield:

D-Arabinose (10323-20-3) → (3S,4R)-5-[N-(benzyloxycarbonyl)amino]-5-deoxypent-2-ulose (121742-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1: isopropylamine; ATA₂₅₆ transaminase; pyridoxal 5'-phosphate / 48 h / 50 °C / pH 8 / Enzymatic reaction

2: sodium hydrogencarbonate / water; 1,4-dioxane / 16 h / 20 °C

3: G_. oxydans DSM 2003 cells / water / 16 h / 35 °C / pH 6.8 / Microbiological reaction

With pyridoxal 5'-phosphate; ATA₂₅₆ transaminase; sodium hydrogencarbonate; isopropylamine; In 1,4-dioxane; water;

DOI:10.1039/d1cy00698c

upstream raw materials:

dihydroxyacetone phosphate

N-benzyloxycarbonylglycinal

dihydroxyacetone

D-Arabinose

Downstream raw materials:

(2S,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol

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

Refernces

• 1、 Gutierrez, Mariana,Parella, Teodor,Joglar, Jesus,Bujons, Jordi,Clapes, Pere. "Structure-guided redesign of d-fructose-6-phosphate aldolase from E. coli: Remarkable activity and selectivity towards acceptor substrates by two-point mutation". supporting information; experimental part. p. 5762 - 5764. Retrieved 2011/07/08.
• 2、 Pederson, Richard L.,Wong, Chi-Huey. "ENZYMATIC ALDOL CONDENSATION AS A ROUTE TO HETEROCYCLES: SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL, FAGOMINE, 1-DEOXYNOJIRIMYCIN AND 1-DEOXYMANNOJIRIMYCIN". . p. 477 - 480. Retrieved 2007/10/02.