3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

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Chemical Name:3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal
CAS No.:250279-61-9
Molecular Formula:C₁₆H₂₀F₃N₃O₂S₂
Molecular Weight:407.481
Hs Code.:

Synonyms:3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

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Chemical Property of 3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

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Technology Process of 3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

There total 8 articles about 3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal 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: 38.0%

: 250279-77-7
Trifluoro-methanesulfonic acid (1S,2S,3S)-3-azido-2-benzyloxy-4-[1,3]dithian-2-yl-1-trifluoromethyl-butyl ester

: 250279-61-9
3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

Guidance literature:: With 15-crown-5; sodium nitrite; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1016/S0008-6215(99)00126-3

Reference yield:

: ((2S,3S)-3-Azido-2-benzyloxy-4-[1,3]dithian-2-yl-1-trifluoromethyl-butoxy)-trimethyl-silane

: 250279-62-0
3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-D-ribo-hexose propane-1,3-diyl dithioacetal

: 250279-61-9
3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

Guidance literature:: With tetrabutyl ammonium fluoride; In various solvent(s); at 0 ℃; for 0.166667h;
DOI:10.1016/S0008-6215(99)00126-3

Reference yield:

: 114071-63-5
methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-α-D-erythro-pentofuranoside

: 250279-61-9
3-azido-4-O-benzyl-2,3-dideoxy-6,6,6-trifluoro-L-lyxo-hexose propane-1,3-diyl dithioacetal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 87 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 1.17 h / 50 °C

2.1: 77 percent / NaH (in oil) / dimethylformamide / 4 h / 0 °C

3.1: 85 percent / Bu₄NF*3H₂O / various solvent(s) / 1.5 h / 20 °C

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.67 h / -78 °C

4.2: 3.08 g / ethyldiisopropylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

5.1: Bu₄NF*3H₂O / various solvent(s) / 0.17 h / -40 °C

6.1: Bu₄NF*3H₂O / various solvent(s) / 0.17 h / 0 °C

7.1: 593 mg / pyridine / CH₂Cl₂ / 1 h / 0 °C

8.1: 38 percent / NaNO₂; 15-crown-5 / dimethylformamide / 4 h / 20 °C

With pyridine; oxalyl dichloride; 15-crown-5; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; sodium nitrite; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: Etherification / 3.1: Substitution / 4.1: Swern oxidation / 4.2: Hydrolysis / 5.1: Addition / 6.1: desilylation / 7.1: Esterification / 8.1: Substitution;
DOI:10.1016/S0008-6215(99)00126-3