9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS No.: 171192-42-0
• Molecular Formula: C₄₆H₆₀O₈Si
• Molecular Weight: 769.063
• Mol file: 171192-42-0.mol

Synonyms:9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property of 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

There total 5 articles about 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester 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%

8-methoxycarbonyloctyl 2,4-di-O-benzyl-β-D-mannopyranoside (134040-47-4) + tert-butylchlorodiphenylsilane (58479-61-1) → 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (171192-42-0)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 2h;

DOI:10.1002/chem.19970030315

Reference yield:

methyl 9-hydroxynonanoate (34957-73-8) → 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (171192-42-0)

Guidance literature:

Multi-step reaction with 3 steps

1: silver silicate, MS 4A / CH₂Cl₂; toluene / 72 h / -40 - 0 °C

2: 86 percent / aq. p-TsOH / 10percent Pd/C / methanol / 4 h / 60 °C

3: 88 percent / imidazole / tetrahydrofuran / 2 h

With 1H-imidazole; silver silicate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/chem.19970030315

Reference yield:

3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate (86032-57-7) → 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (171192-42-0)

Guidance literature:

Multi-step reaction with 4 steps

1: TiBr₄, AcONa / CH₂Cl₂; ethyl acetate; acetonitrile / 3 h

2: silver silicate, MS 4A / CH₂Cl₂; toluene / 72 h / -40 - 0 °C

3: 86 percent / aq. p-TsOH / 10percent Pd/C / methanol / 4 h / 60 °C

4: 88 percent / imidazole / tetrahydrofuran / 2 h

With 1H-imidazole; silver silicate; sodium acetate; titanium(IV) bromide; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile;

DOI:10.1002/chem.19970030315

upstream raw materials:

8-methoxycarbonyloctyl 2,4-di-O-benzyl-β-D-mannopyranoside

tert-butylchlorodiphenylsilane

methyl 9-hydroxynonanoate

3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate

Downstream raw materials:

8-Methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-mannopyranoside

8-Methoxycarbonyloctyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-β-D-mannopyranoside