4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

Base Information

Chemical Name:4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol
CAS No.:135735-93-2
Molecular Formula:C₂₃H₂₆O₄
Molecular Weight:366.457
Hs Code.:

Synonyms:4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

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Chemical Property of 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

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Technology Process of 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

There total 13 articles about 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol 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:

: 135735-94-3,141661-67-8
(1R,2R,3S,4R,5R)-4-O-Acetyl-3-O-benzyl-5-benzyloxymethyl-cyclohexan-1,2,3,4-tetraol

: 135735-93-2
4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

Guidance literature:: With 1,1'-Thiocarbonyldiimidazole; phosphorous acid trimethyl ester; Yield given. Multistep reaction; 1.) toluene, reflux, 2.) reflux;
DOI:10.1039/c39910000756

Reference yield:

: 130021-74-8
(1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

: 135735-93-2
4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH, 2.) (n-Bu)4NI / 1.) THF, 0 deg C, 1 h, 2.) rt, 40 h

2: 1.) 9-BBN, 2.) 3M aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, rt, 24 h, 2.) rt, overnight

3: 97 percent / pyridine, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

4: 96 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

5: toluene / 24 h / Heating

6: (OMe)3P / 72 h / Heating

With pyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; water; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; phosphorous acid trimethyl ester; In dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)88756-1

Reference yield:

: 135735-90-9
(1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol

: 135735-93-2
4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 9-BBN, 2.) 3M aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, rt, 24 h, 2.) rt, overnight

2: 97 percent / pyridine, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

3: 96 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

4: toluene / 24 h / Heating

5: (OMe)3P / 72 h / Heating

With pyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; water; dihydrogen peroxide; trifluoroacetic acid; phosphorous acid trimethyl ester; In dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)88756-1