1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

Base Information

Chemical Name:1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose
CAS No.:250279-64-2
Molecular Formula:C₁₅H₁₆F₃N₃O₄
Molecular Weight:359.305
Hs Code.:

Synonyms:1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

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Chemical Property of 1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

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Technology Process of 1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

There total 9 articles about 1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose 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: 78.0%

: 108-24-7
acetic anhydride

: (4S,5S,6R)-4-Azido-5-benzyloxy-6-trifluoromethyl-tetrahydro-pyran-2-ol

: 250279-64-2
1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

Guidance literature:: With pyridine; at 20 ℃; for 15h;
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

: 250279-64-2
1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

Guidance literature:: Multi-step reaction with 10 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

9.1: 1.51 g / CaCO₃; Hg(ClO₄)2*3H₂O / H₂O; various solvent(s) / 1 h / 20 °C

10.1: 78 percent / pyridine / 15 h / 20 °C

With pyridine; mercury(II) perchlorate; oxalyl dichloride; 15-crown-5; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; calcium carbonate; sodium nitrite; In dichloromethane; water; 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 / 9.1: Cyclization / 10.1: Acetylation;
DOI:10.1016/S0008-6215(99)00126-3

Reference yield:

: 250279-59-5
3-azido-4-O-benzyl-2,3-dideoxy-D-erythro-pentose propane-1,3-diyl dithioacetal

: 250279-64-2
1-O-acetyl-3-azido-4-O-benzyl-2,3,6-trideoxy-6,6,6-trifluoro-L-lyxo-hexopyranose

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 3.08 g / ethyldiisopropylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

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

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

4.1: 593 mg / pyridine / CH₂Cl₂ / 1 h / 0 °C

5.1: 38 percent / NaNO₂; 15-crown-5 / dimethylformamide / 4 h / 20 °C

6.1: 1.51 g / CaCO₃; Hg(ClO₄)2*3H₂O / H₂O; various solvent(s) / 1 h / 20 °C

7.1: 78 percent / pyridine / 15 h / 20 °C

With pyridine; mercury(II) perchlorate; oxalyl dichloride; 15-crown-5; tetrabutyl ammonium fluoride; dimethyl sulfoxide; calcium carbonate; sodium nitrite; In dichloromethane; water; N,N-dimethyl-formamide; 1.1: Swern oxidation / 1.2: Hydrolysis / 2.1: Addition / 3.1: desilylation / 4.1: Esterification / 5.1: Substitution / 6.1: Cyclization / 7.1: Acetylation;
DOI:10.1016/S0008-6215(99)00126-3