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
Hs Code.:

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

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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

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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%

: 84851-94-5
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

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

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:

: 77144-67-3
DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

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

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:

: 77144-72-0
(1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene

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

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