(3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose

Base Information

• Chemical Name: (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose
• CAS No.: 121742-14-1
• Molecular Formula: C₁₄H₁₉NO₆
• Molecular Weight: 297.308
• Mol file: 121742-14-1.mol

Synonyms:(3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose

Chemical Property of (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose

There total 6 articles about (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-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: 79.0%

dihydroxyacetone (96-26-4,26776-70-5) + 3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose (121742-14-1)

Guidance literature:

3-[(N-benzyloxycarbonyl)amino]propanol; With NADH oxidase; horse liver alcohol dehydrogenase; Enzymatic reaction;

dihydroxyacetone; With D-fructose-6-phosphate aldolase from E_. coli A₁₂₉S variant; Enzymatic reaction;

DOI:10.1039/c5ra14414k

Reference yield: 69.0%

dihydroxyacetone (96-26-4,26776-70-5) + 3-[(benzyloxycarbonyl)amino]propanal (65564-05-8) → (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose (121742-14-1)

Guidance literature:

With D-fructose-6-phosphate aldolase; aq. boric/borate buffer; In N,N-dimethyl-formamide; at 4 ℃; for 24h; pH=7.0;

DOI:10.1021/ol0625482

Reference yield:

3-[(benzyloxycarbonyl)amino]propanal (65564-05-8) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 6-[(benzyloxycarbonyl)amino]-5,6-dideoxy-2-hexulose + (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose (121742-14-1)

Guidance literature:

With rabbit muscle aldolase; Shigella flexneri acid phosphatase; L-glycerol-3-phosphate oxidase; catalase; In water; dimethyl sulfoxide; at 20 ℃; for 12h; pH=6; optical yield given as %de; diastereoselective reaction; Enzymatic reaction;

DOI:10.1039/c1gc15429j

upstream raw materials:

dihydroxyacetone phosphate

3-[(benzyloxycarbonyl)amino]propanal

dihydroxyacetone

3-[(N-benzyloxycarbonyl)amino]propanol

Downstream raw materials:

D-fagomine

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