methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside

Base Information

• Chemical Name: methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside
• CAS No.: 302589-69-1
• Molecular Formula: C₇₂H₇₈O₁₀Si
• Molecular Weight: 1131.49
• Mol file: 302589-69-1.mol

Synonyms:methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside

Chemical Property of methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside

There total 4 articles about methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside 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: 81.0%

2,6-anhydro-3,4,5-tri-O-benzyl-7-O-tert-butyldiphenylsilyl-aldehydo-D-glycero-L-manno-heptose (216485-34-6) + (methyl 2,3,4-tri-O-benzyl-6-deoxy-D-galactopyranosid-6-yl)triphenylphosphonium iodide → methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside (302589-69-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -20 ℃; for 4h;

DOI:10.1016/S0040-4039(00)01112-6

Reference yield:

(2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran (305834-18-8) → methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside (302589-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / 4 h / 120 °C

2: 81 percent / n-BuLi; 4 Angstroem molecular sieves / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 4 h / -20 °C

With n-butyllithium; 4 A molecular sieve; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; 2: Wittig reaction;

DOI:10.1021/jo011142u

Reference yield:

3-Methyl-2-[(2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-2,3-dihydro-benzothiazole → methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-13-O-tert-butyldiphenylsilyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranoside (302589-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AgNO₃ / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

2: 81 percent / n-BuLi; 4 Angstroem molecular sieves / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 4 h / -20 °C

With n-butyllithium; 4 A molecular sieve; silver nitrate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetonitrile; 2: Wittig reaction;

DOI:10.1021/jo011142u

upstream raw materials:

2,6-anhydro-3,4,5-tri-O-benzyl-7-O-tert-butyldiphenylsilyl-aldehydo-D-glycero-L-manno-heptose

(2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

Downstream raw materials:

methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-6,7-dideoxy-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranose

methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-6,7,13-trideoxy-13-iodo-α-D-glycero-L-manno-D-galacto-tridec-6(Z)-eno-1,5-pyranose