Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 849611-26-3
• Molecular Formula: C₄₅H₄₉NO₈Si
• Molecular Weight: 759.971
• Mol file: 849611-26-3.mol

Synonyms:Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-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)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

There total 6 articles about Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-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: 82.0%

((2R,3aS,5R,6R,6aS)-6-Benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane + benzyl 2-hydroxyethylcarbamate (77987-49-6) → Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (849611-26-3)

Guidance literature:

With N-iodo-succinimide; ytterbium(III) triflate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1039/b413694b

Reference yield:

(2R,3aS,5R,6R,6aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol → Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (849611-26-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; DMAP / 12 h

2: NaH / dimethylformamide

3: 82 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; N-iodo-succinimide; sodium hydride; triethylamine; ytterbium(III) triflate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b413694b

Reference yield:

(2R,3aS,5R,6R,6aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol → Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (849611-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide

2: 82 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 0 °C

With N-iodo-succinimide; sodium hydride; ytterbium(III) triflate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b413694b

upstream raw materials:

benzyl 2-hydroxyethylcarbamate

benzyl bromide

tert-butylchlorodiphenylsilane

3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

Downstream raw materials:

C₆₄H₆₇NO₁₃Si

2-(N-benzyloxycarbonyl)aminoethyl 5-O-{(2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-(1->5)}-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside