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

Base Information

• Chemical Name: 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
• CAS No.: 328046-75-9
• Molecular Formula: C₅₄H₆₄O₁₅
• Molecular Weight: 953.093
• Mol file: 328046-75-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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: 72.0%

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 (328046-74-8) → 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 (328046-75-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/ol0002976

Reference yield:

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) → 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 (328046-75-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.03 g / NaOMe / methanol / 2 h / 20 °C

2: 87 percent / NaH / dimethylformamide / 3 h / 20 °C

3: 92 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

4: 4 Angstroem molecular sieves; NIS; TFOH / CH₂Cl₂ / 48 h / 20 °C

5: 0.56 g / NaOMe / methanol / 2 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo010180a

Reference yield:

ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside (328046-72-6) → 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 (328046-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

2: 4 Angstroem molecular sieves; NIS; TFOH / CH₂Cl₂ / 48 h / 20 °C

3: 0.56 g / NaOMe / methanol / 2 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo010180a

upstream raw materials:

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

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

benzyl bromide

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