1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-1-enitol

Base Information

Chemical Name:1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-1-enitol
CAS No.:141410-23-3
Molecular Formula:C₁₇H₂₄O₇S
Molecular Weight:372.439
Hs Code.:

Synonyms:1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-1-enitol

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Chemical Property of 1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-1-enitol

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Technology Process of 1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-1-enitol

There total 10 articles about 1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-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: 75.0%

: 141436-58-0,126113-84-6
(-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 141410-23-3
1,2-Dideoxy-4,5-O-isopropylidene-7-O-p-toluenesulfonyl-D-allo-hept-1-enitol

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 18h;
DOI:10.1016/0008-6215(92)84055-W

Reference yield:

: 141410-43-7
benzyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

: 141410-23-3
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(4S,5R)-5-((S)-1-hydroxy-allyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / CaSO₄ / p-toluenesulfonic acid / 15 h / Ambient temperature

2: 93 percent / hydrogen / 10percent Pd/C, NaHCO₃ / methanol / 24 h / 760 Torr

3: 1.) BuLi / 1.) THF, hexane, -5 deg C, 1 h; 2.) THF, r.t., 36 h

4: 91 percent / Bu₄NF / tetrahydrofuran

5: pyridine / CH₂Cl₂

With pyridine; calcium sulfate; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0008-6215(92)84055-W

Reference yield:

: 141410-44-8
benzyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside

: 141410-23-3
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(4S,5R)-5-((S)-1-hydroxy-allyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / hydrogen / 10percent Pd/C, NaHCO₃ / methanol / 24 h / 760 Torr

2: 1.) BuLi / 1.) THF, hexane, -5 deg C, 1 h; 2.) THF, r.t., 36 h

3: 91 percent / Bu₄NF / tetrahydrofuran

4: pyridine / CH₂Cl₂

With pyridine; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0008-6215(92)84055-W