allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Base Information

Chemical Name:allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside
CAS No.:152756-68-8
Molecular Formula:C₂₄H₂₆F₃N₃O₇S
Molecular Weight:557.548
Hs Code.:

Synonyms:allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

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Chemical Property of allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

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Technology Process of allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

There total 4 articles about allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside 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: 82.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 152756-67-7
allyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

: 152756-68-8
allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; at -20 ℃;
DOI:10.1016/0008-6215(93)84029-6

Reference yield:

: 129840-37-5
1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol

: 152756-68-8
allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1) NaN₃, ceric ammonium nitrate, 2) NaNO₂ / 1) MeCN, -40 deg C, 24 h, 2) dioxan, H₂O, 75 deg C, 8 h

2: 39 percent / NaH / dimethylformamide / 6 h / -30 °C

3: 89 percent / 1 M AcOH, 1 M Bu₄NF / tetrahydrofuran / 1 h / -10 deg C to r.t.

4: 82 percent / pyridine / CH₂Cl₂ / -20 °C

With pyridine; sodium azide; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; sodium nitrite; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(93)84029-6

Reference yield:

: 2-azido-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-D-glucopyranose

: 152756-68-8
allyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 39 percent / NaH / dimethylformamide / 6 h / -30 °C

2: 89 percent / 1 M AcOH, 1 M Bu₄NF / tetrahydrofuran / 1 h / -10 deg C to r.t.

3: 82 percent / pyridine / CH₂Cl₂ / -20 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(93)84029-6