5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

Base Information

Chemical Name:5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose
CAS No.:518332-48-4
Molecular Formula:C₄₇H₆₀O₁₃
Molecular Weight:832.986
Hs Code.:

Synonyms:5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

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Chemical Property of 5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

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Technology Process of 5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

There total 11 articles about 5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose 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:

: (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5S)-2-Benzyl-4,5-dihydroxy-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3,4-diol

: 97-72-3
2-Methylpropionic anhydride

: 518332-48-4
5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

Guidance literature:: With dmap; triethylamine; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1021/ol0602710

Reference yield:

: 795305-86-1
phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside

: 518332-48-4
5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 10 steps

1: 92 percent / NaH / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

2: 74 percent / m-CPBA / CH₂Cl₂ / 0.5 h / -78 °C

3: 78 percent / molecular sieves 4 Angstroem; DTBMP; Tf₂O / diethyl ether / 8 h / -78 °C

4: 85 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

5: DMSO; pyridine; TFA / CH₂Cl₂ / 0.5 h / 20 °C

6: 19 mg / tetrahydrofuran / 0.5 h / 20 °C

7: 100 percent / DMAP / acetonitrile / 4 h / 20 °C

8: 93 percent / Bu₃SnH; AIBN / benzene / 0.5 h / Heating

9: aq. TFA / 0.08 h / 20 °C

10: 0.51 g / Et₃N; DMAP / acetonitrile / 2 h / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ol0602710

Reference yield:

: 795305-88-3
phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside

: 518332-48-4
5-deoxy-5-phenyl-3-O-(2,6-di-O-benzyl-3,4-di-O-isobutyryl-α-D-glucopyranosyl)-1,2-O-isobutyryl-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 9 steps

1: 74 percent / m-CPBA / CH₂Cl₂ / 0.5 h / -78 °C

2: 78 percent / molecular sieves 4 Angstroem; DTBMP; Tf₂O / diethyl ether / 8 h / -78 °C

3: 85 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

4: DMSO; pyridine; TFA / CH₂Cl₂ / 0.5 h / 20 °C

5: 19 mg / tetrahydrofuran / 0.5 h / 20 °C

6: 100 percent / DMAP / acetonitrile / 4 h / 20 °C

7: 93 percent / Bu₃SnH; AIBN / benzene / 0.5 h / Heating

8: aq. TFA / 0.08 h / 20 °C

9: 0.51 g / Et₃N; DMAP / acetonitrile / 2 h / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ol0602710