2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate
CAS No.:168138-19-0
Molecular Formula:C₃₀H₃₁Cl₃N₂O₇
Molecular Weight:637.944
Hs Code.:

Synonyms:2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

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Chemical Property of 2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

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Technology Process of 2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

There total 12 articles about 2,4,6-tri-O-benzyl-3-O-carbamoyl-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: 92.0%

: 545-06-2
trichloroacetonitrile

: 2,4,6-tri-O-benzyl-3-O-carbamoyl-D-mannopyranose

: 168138-19-0
2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene;
DOI:10.1016/0040-4039(94)02458-N

Reference yield:

: 13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5
phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

: 168138-19-0
2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 10 steps

1: NH₃ / methanol / Ambient temperature

2: HBF₄*OEt₂ / dimethylformamide / Ambient temperature

3: 1.) n-Bu₂SnO, 2.) CsF

4: 90 percent / conc. H₂SO₄ / methanol / 0.5 h / 0 °C

5: 99 percent / NaH / dimethylformamide

6: 83 percent / DDQ / CH₂Cl₂; H₂O

7: Et₃N, DMAP / tetrahydrofuran / 6 h / Ambient temperature

8: NH₃ / 1 h / 0 °C

9: 74 percent / NBS / acetone; H₂O

10: 92 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With dmap; tetrafluoroboric acid diethyl ether; N-Bromosuccinimide; sulfuric acid; ammonia; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(97)00360-8

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0
(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 168138-19-0
2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 9 steps

1: HBF₄*OEt₂ / dimethylformamide / Ambient temperature

2: 1.) n-Bu₂SnO, 2.) CsF

3: 90 percent / conc. H₂SO₄ / methanol / 0.5 h / 0 °C

4: 99 percent / NaH / dimethylformamide

5: 83 percent / DDQ / CH₂Cl₂; H₂O

6: Et₃N, DMAP / tetrahydrofuran / 6 h / Ambient temperature

7: NH₃ / 1 h / 0 °C

8: 74 percent / NBS / acetone; H₂O

9: 92 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With dmap; tetrafluoroboric acid diethyl ether; N-Bromosuccinimide; sulfuric acid; ammonia; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(97)00360-8