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

Base Information

• Chemical Name: DL-Di-O-acetyl-3,7-O-benzylidene-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol
• CAS No.: 84851-95-6
• Molecular Formula: C₁₈H₁₉N₃O₆
• Molecular Weight: 373.365
• Mol file: 84851-95-6.mol

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

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

There total 7 articles about DL-Di-O-acetyl-3,7-O-benzylidene-(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: 87.0%

DL-Di-O-acetyl-1,7-O-benzylidene-5-O-(methylsulfonyl)-(1,3,4/2,5,6)-4-azido-6-(hydroxymethyl)-1,2,3,5-cyclohexanetetrol (84851-94-5) → DL-Di-O-acetyl-3,7-O-benzylidene-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (84851-95-6)

Guidance literature:

With 1,8-diaza-bicyclo-[5.4.0]-undec-5-ene; In toluene; for 4.5h; Heating;

DOI:10.1021/jo00156a012

Reference yield:

DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol (77144-67-3) → DL-Di-O-acetyl-3,7-O-benzylidene-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (84851-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent

2: 60 percent / MCPBA, phosphate buffer / 1,2-dichloro-ethane / 66 h / 50 °C

3: 62 percent / sodium azide, NH₄Cl, aqueous 2-methoxyethanol / 4.5 h / 80 °C

4: 74 percent / pyridine / 44 h / Ambient temperature

5: 87 percent / 1,8-diazabicyclo<5.4.0>undec-5-ene / toluene / 4.5 h / Heating

With sodium azide; phosphate buffer; 1,8-diaza-bicyclo-[5.4.0]-undec-5-ene; 2-methoxy-ethanol; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In pyridine; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo00156a012

Reference yield:

(1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene (77144-72-0) → DL-Di-O-acetyl-3,7-O-benzylidene-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (84851-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / MCPBA, phosphate buffer / 1,2-dichloro-ethane / 66 h / 50 °C

2: 62 percent / sodium azide, NH₄Cl, aqueous 2-methoxyethanol / 4.5 h / 80 °C

3: 74 percent / pyridine / 44 h / Ambient temperature

4: 87 percent / 1,8-diazabicyclo<5.4.0>undec-5-ene / toluene / 4.5 h / Heating

With sodium azide; phosphate buffer; 1,8-diaza-bicyclo-[5.4.0]-undec-5-ene; 2-methoxy-ethanol; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In pyridine; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo00156a012

upstream raw materials:

DL-Di-O-acetyl-1,7-O-benzylidene-5-O-(methylsulfonyl)-(1,3,4/2,5,6)-4-azido-6-(hydroxymethyl)-1,2,3,5-cyclohexanetetrol

DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

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

(1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene

Downstream raw materials:

valienamine

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