5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

Base Information

Chemical Name:5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose
CAS No.:395666-14-5
Molecular Formula:C₂₄H₂₄N₂O₁₁
Molecular Weight:516.461
Hs Code.:

Synonyms:5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

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Chemical Property of 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

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Technology Process of 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

There total 7 articles about 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-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: 100.0%

: 99-34-3
3,5-dinitrobenzoic acid

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

: 395666-14-5
5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 22h;
DOI:10.1081/CAR-100106928

Reference yield:

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

: 395666-14-5
5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

Guidance literature:: Multi-step reaction with 7 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

7.1: 100 percent / PPh₃; DEAD / tetrahydrofuran / 22 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; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 7.1: Mitsunobu reaction;
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

: 395666-14-5
5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-4-O-(3,5-dinitrobenzoyl)-α-L-erythro-hexulopyranose

Guidance literature:: Multi-step reaction with 5 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

5: 100 percent / PPh₃; DEAD / tetrahydrofuran / 22 h / 20 °C

With sodium hydroxide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 5: Mitsunobu reaction;
DOI:10.1081/CAR-100106928