(1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate

Base Information

• Chemical Name: (1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate
• CAS No.: 80227-27-6
• Molecular Formula: C₁₄H₁₉NO₇
• Molecular Weight: 313.307
• Mol file: 80227-27-6.mol

Synonyms:(1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate

Chemical Property of (1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate

There total 35 articles about (1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate 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%

(3aS,4R,7S,7aS)-7-azido-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxol-4-yl benzoate + acetic anhydride (108-24-7) → (1S,2S,3R,6S)-6-acetamidocyclohex-4-ene-1,2,3-triyl triacetate (80227-27-6)

Guidance literature:

(3aS,4R,7S,7aS)-7-azido-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxol-4-yl benzoate; With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1h; Inert atmosphere;

With acetic acid; In water; at 50 ℃; for 22h; Inert atmosphere;

acetic anhydride; With pyridine; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.9b01221

Reference yield: 72.0%

acetic anhydride (108-24-7) + (+/-)-(1RS,2SR,3SR,4RS)-4-aminocyclohex-5-ene-1,2,3-triol (79435-30-6,89615-00-9,138513-21-0,139626-79-2,139626-80-5,141269-14-9,142796-97-2,142797-00-0,155239-00-2,155239-06-8,157752-14-2,183182-27-6,313217-51-5) → (+/-)-(1RS,2SR,3SR,4RS)-4-(acetylamino)cyclohex-5-ene-1,2,3-triyl triacetate (78776-00-8,80227-27-6,92619-26-6,123808-77-5)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 20h;

DOI:10.1002/hlca.200590220

Reference yield:

Acetic acid (1S,2S,6S)-2-acetoxy-6-tert-butoxycarbonylamino-cyclohex-3-enyl ester → r-1-Acetamido-2-cyclohexen-c-4,t-5,c-6-triyltriacetat (78776-00-8,80227-27-6,92619-26-6,123808-77-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 7 h / 45 °C

2: n-BuLi / tetrahydrofuran / 16 h / Ambient temperature

3: pyridine, DMAP / 16 h

4: 88 percent / aq. H₂O₂, iPr₂NEt / 1.) 0 deg C, CH₂Cl₂, 15 min, 2.) THF, 50 deg C, 1.5 h

5: 1.) aq. HCl, 2.) NH₃/MeOH / 1.) THF, reflux, 3 h, 2.) 2-3 h

6: pyridine, DMAP / 16 h

With pyridine; hydrogenchloride; methanol; dmap; n-butyllithium; ammonia; dihydrogen peroxide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo971907r

upstream raw materials:

acetic anhydride

(+/-)-(1RS,2SR,3SR,4RS)-4-aminocyclohex-5-ene-1,2,3-triol

(+/-)-conduramine A-1

(+/-)-1-p-toluenesulfonyl-5-tert-butoxycarbonylamino-1,3-cyclohexadiene

Downstream raw materials:

Konduramin F₁-hydrochlorid

2,3-Diamino-2,3-didesoxy-muco-inosit, Dihydrochlorid

2-Acetamido-1,3,5,6-tetra-O-acetyl-2,4-didesoxy-4-dimethylamino-muco-inositol

2-Acetamido-1,4,5,6-tetra-O-acetyl-2,3-didesoxy-3-dimethylamino-muco-inositol