Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 1053268-95-3
• Molecular Formula: C₆₄H₆₈O₁₄
• Molecular Weight: 1061.24

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 14 articles about Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl 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:

D-fructose (470-23-5,470-24-6,10247-46-8,10489-79-9,35673-97-3,36441-90-4,36441-92-6,36468-68-5,37500-17-7,40461-86-7,40461-87-8,41579-20-8,41846-98-4,41846-99-5,41847-00-1,41847-01-2,41847-02-3,41847-03-4,41847-04-5,41847-05-6,41847-06-7,41847-51-2,41847-52-3,42744-42-3) → Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (1053268-95-3)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂SO₄

2: 55 percent / pyridine / 3 h / 20 °C

3: 60 percent / pyridine

4: TBAF / tetrahydrofuran / 1 h

5: NaH / dimethylformamide / 1 h

6: 47 mg / TFA; Et₃SiH / CH₂Cl₂ / 1 h

7: 86 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

8: 93 percent / tris(dimethylaminosulfonium) difluorotrimethylsilicate / dimethylformamide / 1 h

9: pyridine; 4-DMAP / 60 °C

With pyridine; triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo020341q

Reference yield:

methyl 6-O-(tert-butyldimethylsilyl)-β-D-fructofuranoside (147672-51-3) → Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (1053268-95-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 percent / pyridine

2: TBAF / tetrahydrofuran / 1 h

3: NaH / dimethylformamide / 1 h

4: 47 mg / TFA; Et₃SiH / CH₂Cl₂ / 1 h

5: 86 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

6: 93 percent / tris(dimethylaminosulfonium) difluorotrimethylsilicate / dimethylformamide / 1 h

7: pyridine; 4-DMAP / 60 °C

With pyridine; triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo020341q

Reference yield:

methyl β-D-fructofuranoside (13403-14-0,15219-93-9,16975-88-5,51295-55-7,51295-56-8,52443-09-1,60504-77-0,60504-79-2,63526-47-6,69460-17-9,92283-23-3) → Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (1053268-95-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 55 percent / pyridine / 3 h / 20 °C

2: 60 percent / pyridine

3: TBAF / tetrahydrofuran / 1 h

4: NaH / dimethylformamide / 1 h

5: 47 mg / TFA; Et₃SiH / CH₂Cl₂ / 1 h

6: 86 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

7: 93 percent / tris(dimethylaminosulfonium) difluorotrimethylsilicate / dimethylformamide / 1 h

8: pyridine; 4-DMAP / 60 °C

With pyridine; triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo020341q

upstream raw materials:

4,4'-dimethoxytrityl chloride

methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

D-fructose

methyl 6-O-(tert-butyldimethylsilyl)-β-D-fructofuranoside

Downstream raw materials:

methyl 6-O-acetyl-4-O-benzoyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

methyl 3-O-benzyl-β-D-fructofuranosyl-(2-1)-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

methyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl-(2-1)-6-O-acetyl-4-O-benzoyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

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