5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

Base Information

Chemical Name:5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose
CAS No.:395666-13-4
Molecular Formula:C₁₇H₂₂O₆
Molecular Weight:322.358
Hs Code.:

Synonyms:5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

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Chemical Property of 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

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Technology Process of 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

There total 6 articles about 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose 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: 71.0%

: 395666-12-3
5-C-benzoyloxymethyl-4-O-tert-butyldiphenylsilyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

: 395666-13-4
5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1081/CAR-100106928

Reference yield:

: 3-deoxy-1,2-O-isopropylidene-β-D-erythro-hexulopyranose

: 395666-13-4
5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-Bu₂SnO / methanol / 2 h / Heating

1.2: 50 percent / dimethylformamide / 20 h / 20 °C

2.1: 72 percent / PCC; 4 Angstroem molecular sieves; NaOAc / CH₂Cl₂ / 20 °C

3.1: 1.38 g / dimethylsulfoxide; diethyl ether / 2.5 h

4.1: 8.5 percent / BH₃*SMe₂; NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

5.1: 41 percent / Et₃N / CH₂Cl₂ / 20 °C

6.1: 71 percent / TBAF*3H₂O / tetrahydrofuran / 8 h / 20 °C

With sodium hydroxide; dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium acetate; di(n-butyl)tin oxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1081/CAR-100106928

Reference yield:

: 395666-04-3
(5R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-8-one

: 395666-13-4
5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-α-L-threo-hexulopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 1.38 g / dimethylsulfoxide; diethyl ether / 2.5 h

2: 8.5 percent / BH₃*SMe₂; NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

3: 41 percent / Et₃N / CH₂Cl₂ / 20 °C

4: 71 percent / TBAF*3H₂O / tetrahydrofuran / 8 h / 20 °C

With sodium hydroxide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1081/CAR-100106928