Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester
• CAS No.: 204918-60-5
• Molecular Formula: C₄₀H₄₈O₁₃Si
• Molecular Weight: 764.899
• Mol file: 204918-60-5.mol

Synonyms:Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester

There total 13 articles about Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl 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: 79.0%

1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside (204918-48-9) + methyl 2-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside (204918-54-7) → Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester (204918-60-5)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -10 ℃;

DOI:10.1016/S0960-894X(98)00049-3

Reference yield:

tetra-O-acetyl-D-arabinofuranose (61826-42-4) → Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester (204918-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

2: 79 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0 °C

With N-iodo-succinimide; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; In dichloromethane; 1: Substitution / 2: glycosylation;

DOI:10.1021/ja993543l

Reference yield:

methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside (164454-52-8) → Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester (204918-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / pyridine / 0 - 20 °C

2: 76 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

3: 84 percent / pyridine; DMAP / 2.5 h / 0 °C

4: 79 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0 °C

With pyridine; dmap; N-iodo-succinimide; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: desilylation / 3: Substitution / 4: glycosylation;

DOI:10.1021/ja993543l

upstream raw materials:

1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside

methyl 2-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside

benzoyl chloride

methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside