DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

Base Information

• Chemical Name: DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol
• CAS No.: 74708-35-3
• Molecular Formula: C₁₅H₁₉N₃O₈
• Molecular Weight: 369.331
• Mol file: 74708-35-3.mol

Synonyms:DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

Chemical Property of DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

There total 15 articles about DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-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: 93.0%

DL-tetra-O-acetyl-(1,3/2,4)-4-chloro-4-C-hydroxymethyl-5-cyclohexene-1,2,3-triol (81692-16-2,102490-47-1) → DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (74708-35-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 15h;

DOI:10.1246/cl.1982.279

Reference yield:

DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4) → DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (74708-35-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 37 percent / 70percent m-chloroperoxybenzoic acid (mCPBA), NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

2: 100 percent / 12 M HCl / tetrahydrofuran / 1 h / 0 - 5 °C

3: 100 percent / H₂SO₄ / Ambient temperature

4: 93 percent / NaN₃ / dimethylformamide / 15 h / 60 °C

With hydrogenchloride; sodium azide; sulfuric acid; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.56.1161

Reference yield:

Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester (81692-15-1) → DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (74708-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂SO₄ / Ambient temperature

2: 93 percent / NaN₃ / dimethylformamide / 15 h / 60 °C

With sodium azide; sulfuric acid; In N,N-dimethyl-formamide;

DOI:10.1246/bcsj.56.1161

upstream raw materials:

potassium acetate

DL-tri-O-acetyl-(1,3/2,6)-6-bromo-4-bromomethyl-4-cyclohexene-1,2,3-triol

DL-tri-O-acetyl-(1,3,6/2)-6-bromo-4-bromomethyl-4-cyclohexene-1,2,3-triol

DL-Di-O-acetyl-3,7-O-benzylidene-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

Downstream raw materials:

Acetic acid (4aS,5R,6S,7S,8S,8aR)-8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,4R,9aS,9bR)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-7-yl ester

Acetic acid (4aR,5S,6R,7S,8S,8aR)-8-acetoxy-6-hydroxy-2-phenyl-5-((3aR,4R,9aS,9bR)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-7-yl ester

DL-N-<(1SR)-4,7:5,6-di-O-isopropylidene-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexylamine

N-<(1SR)-4,7:5,6-di-O-isopropylidene-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-3,4-di-O-acetyl-5,7-O-benzylidene-(1,3,5/2,4,6)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexylamine

Refernces

• 1、 Ogawa, Seiichiro,Chida, Noritaka,Suami, Tetsuo. "Synthetic Studies on the Validamycins. 5. Synthesis of DL-Hydroxyvalidamine and DL-Valienamine". . p. 1203 - 1207. Retrieved 2007/10/02.