(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

Base Information

Chemical Name:(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
CAS No.:1319152-63-0
Molecular Formula:C₅₄H₆₄Cl₃NO₁₄
Molecular Weight:1057.46
Hs Code.:

Synonyms:(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

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Chemical Property of (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

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Technology Process of (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

There total 6 articles about (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 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: 86.0%

: 1319152-62-9
(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranose

: 545-06-2
trichloroacetonitrile

: 1319152-63-0
(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.carres.2011.05.006

Reference yield:

: 1319152-50-5
phenyl 2,3-di-O-pivaloyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1319152-63-0
(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-THF / tetrahydrofuran / 0.08 h / 0 °C

1.2: 0 - 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -40 - 20 °C / Molecular sieve

3.1: N-iodo-succinimide; trifluoroacetic acid / dichloromethane / 2 h / 0 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

With N-iodo-succinimide; borane-THF; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.carres.2011.05.006

Reference yield:

: 3282-30-2
pivaloyl chloride

: 1319152-63-0
(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine; dmap / dichloromethane / 0 - 70 °C

2.1: borane-THF / tetrahydrofuran / 0.08 h / 0 °C

2.2: 0 - 20 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -40 - 20 °C / Molecular sieve

4.1: N-iodo-succinimide; trifluoroacetic acid / dichloromethane / 2 h / 0 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

With pyridine; dmap; N-iodo-succinimide; borane-THF; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.carres.2011.05.006