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

Base Information

• Chemical Name: thexyldimethylsilyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 679412-26-1
• Molecular Formula: C₅₉H₆₉NO₁₂Si
• Molecular Weight: 1012.28
• Mol file: 679412-26-1.mol

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

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

There total 1 articles about thexyldimethylsilyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-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: 71.0%

dimethylthexylsilyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside + 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 (319922-26-4) → thexyldimethylsilyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-26-1) + thexyldimethylsilyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 0.333333h;

DOI:10.1021/jo0354239

Reference yield: 68.0%

thexyldimethylsilyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-26-1) → thexyldimethylsilyl 2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-36-3)

Guidance literature:

With trans-[Pd(NH₂)2Cl₂]; tert-butyl alcohol; for 12h; Heating;

DOI:10.1021/jo0354239

Reference yield:

thexyldimethylsilyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (679412-26-1) → O-[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-D-glucopyranosyl trichloroacetimidate

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / trans-Pd(NH₃)2Cl₂; t-BuOH / 12 h / Heating

2: 87.5 percent / pyridine / 0.5 h / 0 °C

3: 78 percent / BH₃*THF; Bu₂BOTf / CH₂Cl₂ / 5 h / 0 °C

4: 88 percent / pyridine; DMAP / 2 h / 20 °C

5: 88 percent / HP*pyridine / tetrahydrofuran / 20 °C

6: 74 percent / NaH / CH₂Cl₂ / 0.5 h / 0 °C

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

DOI:10.1021/jo0354239

upstream raw materials:

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

Downstream raw materials:

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

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

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