6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:1220958-06-4
Molecular Formula:C₂₉H₃₁ClN₄O₈
Molecular Weight:599.04
Hs Code.:

Synonyms:6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 13 articles about 6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-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: 92.0%

: 1448540-28-0
4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

: 146292-90-2
6-azidohexan-1-ol

: 1220958-06-4
6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 - 0 ℃; for 1h; Molecular sieve; Inert atmosphere;
DOI:10.1021/jo4012442

Reference yield: 56.0%

: 1220958-05-3
6-azidohexyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 79-04-9
chloroacetyl chloride

: 1220958-06-4
6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.3762/bjoc.6.17

Reference yield:

: 31505-45-0
2-deoxy-2-phthalimido-β-D-glucopyranose

: 1220958-06-4
6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: boron trifluoride diethyl etherate / dichloromethane / 1 h / Reflux

3: sodium methylate / methanol / 3 h / 20 °C

4: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 1.5 h / 70 °C

5: pyridine / dichloromethane / 0.67 h / 0 °C

6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.67 h / 0 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

8: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - 0 °C / Molecular sieve; Inert atmosphere

With pyridine; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo4012442