thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 679412-27-2
• Molecular Formula: C₇₉H₈₃NO₁₆Si
• Molecular Weight: 1330.61
• Mol file: 679412-27-2.mol

Synonyms:thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 7 articles about thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 88.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + thexyldimethylsilyl 2,4-di-O-benzyl-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-38-5) → thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-27-2)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1021/jo0354239

Reference yield:

Phenoxyacetyl chloride (701-99-5) → thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 87.5 percent / pyridine / 0.5 h / 0 °C

2: 78 percent / BH₃*THF; Bu₂BOTf / CH₂Cl₂ / 5 h / 0 °C

3: 88 percent / pyridine; DMAP / 2 h / 20 °C

With pyridine; dmap; borane-THF; di-n-butylboryl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/jo0354239

Reference yield:

dimethylthexylsilyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside → thexyldimethylsilyl 2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / TMSOTf / CH₂Cl₂ / 0.33 h / -50 °C

2: 68 percent / trans-Pd(NH₃)2Cl₂; t-BuOH / 12 h / Heating

3: 87.5 percent / pyridine / 0.5 h / 0 °C

4: 78 percent / BH₃*THF; Bu₂BOTf / CH₂Cl₂ / 5 h / 0 °C

5: 88 percent / pyridine; DMAP / 2 h / 20 °C

With pyridine; dmap; borane-THF; trans-[Pd(NH₂)2Cl₂]; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; tert-butyl alcohol; In dichloromethane;

DOI:10.1021/jo0354239

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

thexyldimethylsilyl 2,4-di-O-benzyl-3-O-phenoxyacetyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Phenoxyacetyl chloride

2,2,2-Trichloro-acetimidic acid (2R,4aR,6R,7S,8S,8aR)-8-allyloxy-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester