methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

Base Information

Chemical Name:methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate
CAS No.:361192-69-0
Molecular Formula:C₄₉H₅₆F₆N₂O₂₂S
Molecular Weight:1171.04
Hs Code.:

methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

Synonyms:methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

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Chemical Property of methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

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Technology Process of methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

There total 12 articles about methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate 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: 84.0%

: 108-98-5
thiophenol

: 361192-67-8
methyl [2,4,7-tri-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

: 361192-69-0
methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

Guidance literature:: With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane;
DOI:10.1021/jo010345f

Reference yield:

: methyl [2-(trimethylsilyl)ethyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α,β-D-galacto-non-2-ulopyranosid]onate

: 361192-69-0
methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / NaOMe / methanol / 2 h

2: 61 percent / CSA / acetonitrile / 1 h

3: 96 percent / pyridine / 16 h

4: 72 percent / BH₃*NMe₂; AlCl₃; molecular sieves 4 Angstroem / tetrahydrofuran / 0 - 20 °C

5: 55 percent / molecular sieves 3 Angstroem; NIS; TfOH / acetonitrile / 0.08 h / -35 °C

6: TFA / 1,2-dichloro-ethane / 2 h

7: DMAP / pyridine / 72 h / 20 °C

8: 84 percent / BF₃*Et₂O / 1,2-dichloro-ethane

With pyridine; dmap; N-iodo-succinimide; aluminium trichloride; trifluorormethanesulfonic acid; dimethylamine borane; 3 A molecular sieve; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo010345f

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 361192-69-0
methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate

Guidance literature:: Multi-step reaction with 7 steps

1: 61 percent / CSA / acetonitrile / 1 h

2: 96 percent / pyridine / 16 h

3: 72 percent / BH₃*NMe₂; AlCl₃; molecular sieves 4 Angstroem / tetrahydrofuran / 0 - 20 °C

4: 55 percent / molecular sieves 3 Angstroem; NIS; TfOH / acetonitrile / 0.08 h / -35 °C

5: TFA / 1,2-dichloro-ethane / 2 h

6: DMAP / pyridine / 72 h / 20 °C

7: 84 percent / BF₃*Et₂O / 1,2-dichloro-ethane

With pyridine; dmap; N-iodo-succinimide; aluminium trichloride; trifluorormethanesulfonic acid; dimethylamine borane; 3 A molecular sieve; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; trifluoroacetic acid; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo010345f