(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

Base Information

Chemical Name:(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane
CAS No.:168138-20-3
Molecular Formula:C₅₁H₅₅NO₁₂
Molecular Weight:873.997
Hs Code.:

Synonyms:(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

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Chemical Property of (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

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Technology Process of (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

There total 20 articles about (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane 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%

: 168138-13-4
(1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-hydroxy-3-butenyl>-2-phenyl-1,3-dioxane

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

: 168138-20-3
(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -15 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(97)00360-8

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

: 168138-20-3
(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 11 steps

1: NH₃ / methanol / Ambient temperature

2: HBF₄*OEt₂ / dimethylformamide / Ambient temperature

3: 1.) n-Bu₂SnO, 2.) CsF / 1.) toluene, reflux, 3 h, 2.) DMF, room temperature, 12 h

4: 94 percent / NaH / dimethylformamide; paraffin / 12 h / Ambient temperature

5: 54 percent / NBS / acetone; H₂O / 0.5 h / Ambient temperature

6: 66 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C -> room temperature

7: 2.32 g / (COCl)2, DMSO, Et₃N / CH₂Cl₂

8: L-Selectride / tetrahydrofuran

9: 94 percent / pyridine / 6 h / Ambient temperature

10: 91 percent / DDQ / CH₂Cl₂; H₂O / 2.5 h / Ambient temperature

11: 82 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / -15 °C

With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; ammonia; L-Selectride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; paraffin;
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

: 168138-20-3
(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 10 steps

1: HBF₄*OEt₂ / dimethylformamide / Ambient temperature

2: 1.) n-Bu₂SnO, 2.) CsF / 1.) toluene, reflux, 3 h, 2.) DMF, room temperature, 12 h

3: 94 percent / NaH / dimethylformamide; paraffin / 12 h / Ambient temperature

4: 54 percent / NBS / acetone; H₂O / 0.5 h / Ambient temperature

5: 66 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C -> room temperature

6: 2.32 g / (COCl)2, DMSO, Et₃N / CH₂Cl₂

7: L-Selectride / tetrahydrofuran

8: 94 percent / pyridine / 6 h / Ambient temperature

9: 91 percent / DDQ / CH₂Cl₂; H₂O / 2.5 h / Ambient temperature

10: 82 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / -15 °C

With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; L-Selectride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; paraffin;
DOI:10.1016/S0040-4020(97)00360-8