6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

Base Information

Chemical Name:6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose
CAS No.:114144-72-8
Molecular Formula:C₁₈H₂₆O₄
Molecular Weight:306.402
Hs Code.:

Synonyms:6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

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Chemical Property of 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

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Technology Process of 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

There total 15 articles about 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose 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: 89.0%

: 113660-85-8
3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

: 100-44-7
benzyl chloride

: 114144-72-8
6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

Guidance literature:: With sodium hydride; In dimethyl sulfoxide; for 20h; Ambient temperature;
DOI:10.1248/cpb.35.2184

Reference yield:

: 26291-75-8,81114-49-0,109200-09-1,128461-80-3
(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 114144-72-8
6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: 1) p-toluenesulfonyl chloride, pyridine; 2) K₂CO₃ / 1) 17 h; 2) MeOH, r.t., 40 min

2: 81 percent / lithium aluminium hydride / diethyl ether / 5 h, 0 deg C, then 1 h r.t.

3: 92 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

4: 100 percent / tetrahydrofuran / 2 h / 18 °C

5: BH₃-THF / tetrahydrofuran / 1 h / 0 - 5 °C

6: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; borane-THF; 3 A molecular sieve; sodium hydride; potassium carbonate; p-toluenesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2184

Reference yield:

: 56982-95-7
(3aR,5S,6R,6aR)-2,2,6-trimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

: 114144-72-8
6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-talofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / lithium aluminium hydride / diethyl ether / 5 h, 0 deg C, then 1 h r.t.

2: 92 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

3: 100 percent / tetrahydrofuran / 2 h / 18 °C

4: BH₃-THF / tetrahydrofuran / 1 h / 0 - 5 °C

5: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

With lithium aluminium tetrahydride; borane-THF; 3 A molecular sieve; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2184