DL-(1,3/2,6)-6-acetamido-4-C-acetoxymethyl-1,2,3-tri-O-acetyl-4-cyclohexene-1,2,3-triol

Base Information

• Chemical Name: DL-(1,3/2,6)-6-acetamido-4-C-acetoxymethyl-1,2,3-tri-O-acetyl-4-cyclohexene-1,2,3-triol
• CAS No.: 38231-89-9
• Molecular Formula: C₁₇H₂₃NO₉
• Molecular Weight: 385.371
• Mol file: 38231-89-9.mol

Synonyms:

Chemical Property of DL-(1,3/2,6)-6-acetamido-4-C-acetoxymethyl-1,2,3-tri-O-acetyl-4-cyclohexene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-(1,3/2,6)-6-acetamido-4-C-acetoxymethyl-1,2,3-tri-O-acetyl-4-cyclohexene-1,2,3-triol

There total 29 articles about DL-(1,3/2,6)-6-acetamido-4-C-acetoxymethyl-1,2,3-tri-O-acetyl-4-cyclohexene-1,2,3-triol 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: 99.0%

acetic anhydride (108-24-7) + valienamine (38231-86-6) → (1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol (74645-52-6,74645-53-7,38231-89-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.tet.2013.06.046

Reference yield:

(5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid ethyl ester → (1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol (74645-52-6,74645-53-7,38231-89-9)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / Ambient temperature

2: n-butyllithium; bidentate phosphite ligand; trimethyltin acetate; palladium diacetate / tetrahydrofuran; hexane / 42 h / Heating

3: methanol; triethanolamine; sodium methylate; diisobutylaluminium hydride; Rochelle's salt

4: hydrogen fluoride / acetonitrile / 16 h / Ambient temperature

5: ammonia; sodium / -78 °C

6: pyridine / Ambient temperature

With pyridine; methanol; n-butyllithium; triethanolamine; bidentate phosphite ligand; trimethyltin acetate; hydrogen fluoride; ammonia; sodium methylate; palladium diacetate; sodium; diisobutylaluminium hydride; sodium hydrogencarbonate; Rochelle's salt; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ja973081g

Reference yield:

(1S,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid ethyl ester → (1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol (74645-52-6,74645-53-7,38231-89-9)

Guidance literature:

Multi-step reaction with 5 steps

1: n-butyllithium; bidentate phosphite ligand; trimethyltin acetate; palladium diacetate / tetrahydrofuran; hexane / 42 h / Heating

2: methanol; triethanolamine; sodium methylate; diisobutylaluminium hydride; Rochelle's salt

3: hydrogen fluoride / acetonitrile / 16 h / Ambient temperature

4: ammonia; sodium / -78 °C

5: pyridine / Ambient temperature

With pyridine; methanol; n-butyllithium; triethanolamine; bidentate phosphite ligand; trimethyltin acetate; hydrogen fluoride; ammonia; sodium methylate; palladium diacetate; sodium; diisobutylaluminium hydride; Rochelle's salt; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/ja973081g

upstream raw materials:

(+)-validoxylamine A

acetic anhydride

valienamine

N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide

Downstream raw materials:

valienamine

(1S,2R,3S,4S,5S,6R)-6-acetamido-4-(acetoxymethyl)-5-bromo-4-hydroxycyclohexane-1,2,3-triyl triacetate

(1S,2R,3S,4S,5S,6R)-6-acetamido-4-(acetoxymethyl)-5-iodo-4-hydroxycyclohexane-1,2,3-triyl triacetate

(1S,2R,3S,4S,5S,6R)-6-acetamido-4-(acetoxymethyl)-5-chloro-4-hydroxycyclohexane-1,2,3-triyl triacetate