Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester
• CAS No.: 328046-70-4
• Molecular Formula: C₄₉H₆₀O₁₃Si
• Molecular Weight: 885.093
• Mol file: 328046-70-4.mol

Synonyms:Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester

There total 5 articles about Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-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: 70.0%

2,3,5-tri-O-acetyl-α,β-D-arabinofuranosyl-trichloroacetamide (328046-69-1) + ethyl 2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside (328046-68-0) → Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester (328046-70-4)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 - 20 ℃; for 2h;

DOI:10.1021/ol0002976

Reference yield:

1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9,43225-70-3) → Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester (328046-70-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / n-Bu₃SnOEt / 1,2-dichloro-ethane / 3 h / Heating

2: 65 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

3: 4 Angstyroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 2 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; tributyltin ethoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo010180a

Reference yield:

ethyl 2,3-di-O-benzyl-β-D-galactofuranoside (76696-18-9) → Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester (328046-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

2: 4 Angstyroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/jo010180a

upstream raw materials:

2,3,5-tri-O-acetyl-α,β-D-arabinofuranosyl-trichloroacetamide

ethyl 2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside

1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose

ethyl 2,3-di-O-benzyl-β-D-galactofuranoside

Downstream raw materials:

(R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol

ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside

ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-2,3-di-O-benzyl-β-D-galactofuranoside

acetic acid 4-acetoxy-2-[2-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-(3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethoxy]-5-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester