3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

Base Information

Chemical Name:3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate
CAS No.:162111-91-3
Molecular Formula:C₃₇H₄₄NO₂₁P
Molecular Weight:869.724
Hs Code.:

Synonyms:3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

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Chemical Property of 3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

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Technology Process of 3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

There total 32 articles about 3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate 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: 84.0%

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 162111-83-3
3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranoside

: 162111-91-3
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1.5h;

Reference yield: 61.0%

: 3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α,β-L-gulopyranoside

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 162111-91-3
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

Guidance literature:: 3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α,β-L-gulopyranoside; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

chlorophosphoric acid diphenyl ester; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

Reference yield:

: 65827-58-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside

: 162111-91-3
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / H₂ / 10percent Pd(OH)2/C / methanol / 10 h / 25 °C / 760 Torr

2: 86 percent / pyridine, DMAP / 2 h / 40 °C

3: 88 percent / 10percent NH₃/THF / CH₂Cl₂ / 1.5 h / 25 °C

4: 78 percent / benzylamine / tetrahydrofuran / 24 h / 25 °C

5: 1.) BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 10 min

6: 93 percent / TMSOTf / CH₂Cl₂ / 0.17 h / 0 °C

7: H₂ / 10percent Pd(OH)2/C / methanol / 15 h / 25 °C / 760 Torr

8: pyridine / 10 h / 25 °C

9: 81 percent / benzylamine / tetrahydrofuran / 17 h / 25 °C

10: 1.) BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 10 min

With tetrahydrofuran; pyridine; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; ammonia; hydrogen; benzylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;