1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Base Information

Chemical Name:1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside
CAS No.:162153-19-7
Molecular Formula:C₄₇H₅₃NO₁₅
Molecular Weight:871.936
Hs Code.:

Synonyms:1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

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Chemical Property of 1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

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Technology Process of 1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

There total 15 articles about 1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside 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: 93.0%

: 78355-19-8
Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside

: 162111-85-5
diphenylphosphoryl-2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranoside

: 162153-19-7
1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.166667h;

Reference yield:

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

: 162153-19-7
1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 73366-73-1
benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

: 162153-19-7
1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / pyridine / 4 h / 25 °C

2: 83 percent / 80percent aq. ACOH / 1 h / 60 °C

3: 85 percent / Ph₃P, imidazole, I₂ / toluene / 3 h / 100 °C

4: 56 percent / AgF, pyridine / 3 h / 25 °C

5: 1.) catecholborane, Rh(PPh₃)3Cl, 2.) aq. NaOH, potassium phosphate monobasic, 50percent aq. H₂O₂ / 1.) THF, 25 deg C, 16 h, 2.) EtOH, THF, 25 deg C, 3 h

6: 72 percent / CF₃SO₃H / CH₂Cl₂; hexane / 1 h / 25 °C

7: 84 percent / K₂CO₃, MeOH / 2 h / 25 °C

8: 93 percent / TMSOTf / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; 1H-imidazole; methanol; sodium hydroxide; potassium dihydrogenphosphate; Wilkinson's catalyst; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; iodine; silver fluoride; potassium carbonate; acetic acid; triphenylphosphine; benzo[1,3,2]dioxaborole; In hexane; dichloromethane; toluene;