benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

Base Information

Chemical Name:benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside
CAS No.:352212-05-6
Molecular Formula:C₅₅H₆₄O₁₈
Molecular Weight:1013.1
Hs Code.:

benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

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Chemical Property of benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

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Technology Process of benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

There total 12 articles about benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside 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:

: (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl)-pentan-2-ol

: 352212-05-6
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent / Dess-Martin-periodinane / CH₂Cl₂

2.1: 62 percent / toluene; tetrahydrofuran / -40 - 20 °C

3.1: 94 percent / TBAF / tetrahydrofuran / 40 °C

4.1: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 69 percent / aq. TFA / tetrahydrofuran / 0.83 h / Heating

6.1: various solvent(s) / 1 h / -80 °C

7.1: 317 mg / pyridine / CH₂Cl₂ / 20 °C

8.1: mCPBA / tetrahydrofuran / 0.25 h / -80 °C

8.2: Ac₂O; NaOAc / tetrahydrofuran / 1.5 h / Heating

9.1: NaOMe / methanol; tetrahydrofuran

9.2: pyridine

10.1: NaClO₂; aq. KH₂PO₄ / acetonitrile; 2-methyl-propan-2-ol; various solvent(s) / 0.67 h / 20 °C

11.1: 150 mg / diethyl ether / 20 °C

With pyridine; sodium chlorite; potassium dihydrogenphosphate; tetrabutyl ammonium fluoride; sodium methylate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo015543l

Reference yield:

: 352211-86-0
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-methylene-D-glycero-D-gulo-non-2-ulos-1-yl]-β-D-galacto-hexopyranoside

: 352212-05-6
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 69 percent / aq. TFA / tetrahydrofuran / 0.83 h / Heating

3.1: various solvent(s) / 1 h / -80 °C

4.1: 317 mg / pyridine / CH₂Cl₂ / 20 °C

5.1: mCPBA / tetrahydrofuran / 0.25 h / -80 °C

5.2: Ac₂O; NaOAc / tetrahydrofuran / 1.5 h / Heating

6.1: NaOMe / methanol; tetrahydrofuran

6.2: pyridine

7.1: NaClO₂; aq. KH₂PO₄ / acetonitrile; 2-methyl-propan-2-ol; various solvent(s) / 0.67 h / 20 °C

8.1: 150 mg / diethyl ether / 20 °C

With pyridine; sodium chlorite; potassium dihydrogenphosphate; sodium methylate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo015543l

Reference yield:

: 352211-87-1
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-Oisopropylidene-2-methylene-D-glycero-D-gulo-non-2-ulos-1-yl]-β-D-galacto-hexopyranoside

: 352212-05-6
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[{methyl-(4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-erythro-L-talo-non-2-yl)onate}-methyl]-β-D-galacto-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 69 percent / aq. TFA / tetrahydrofuran / 0.83 h / Heating

2.1: various solvent(s) / 1 h / -80 °C

3.1: 317 mg / pyridine / CH₂Cl₂ / 20 °C

4.1: mCPBA / tetrahydrofuran / 0.25 h / -80 °C

4.2: Ac₂O; NaOAc / tetrahydrofuran / 1.5 h / Heating

5.1: NaOMe / methanol; tetrahydrofuran

5.2: pyridine

6.1: NaClO₂; aq. KH₂PO₄ / acetonitrile; 2-methyl-propan-2-ol; various solvent(s) / 0.67 h / 20 °C

7.1: 150 mg / diethyl ether / 20 °C

With pyridine; sodium chlorite; potassium dihydrogenphosphate; sodium methylate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo015543l