methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Base Information

Chemical Name:methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate
CAS No.:123170-15-0
Molecular Formula:C₇₉H₈₄N₂O₁₆S
Molecular Weight:1349.61
Hs Code.:

methyl O-<methyl (5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-(phenylthio)-D-erythro-α-L-gluco-2-nonulopyranosid)onate>-(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Synonyms:methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

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Chemical Property of methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

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Technology Process of methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

There total 6 articles about methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 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: 64.0%

: 123284-43-5
Methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-bromo-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

: 123170-14-9
methyl 5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

: 123170-15-0
methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Guidance literature:: With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In tetrachloromethane; 1) -20 deg C, 0.5h, 2) 0 deg C, 1h, 3) RT, 18h;
DOI:10.1021/jo00032a601

Reference yield:

: 25875-99-4,79026-38-3
methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

: 123170-15-0
methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / (+/-)-camphorsulfonic acid / dimethylformamide / 3 h / Ambient temperature

2: 1) CaH₂, Bu₄NI, KOH / 1a) THF, DMSO, 0 deg C, 4h, 1b) RT, 16h, 2) ether

3: 83 percent / BH₃*NMe₃, AlCl₃, molecular sieve 4A / tetrahydrofuran / 1) 0 deg C, 0.5h, 2) RT, 2h

4: 64 percent / Hg(CN)2, HgBr₂, molecular sieve 4A / CCl₄ / 1) -20 deg C, 0.5h, 2) 0 deg C, 1h, 3) RT, 18h

With potassium hydroxide; aluminium trichloride; calcium hydride; trimethylamine-borane; 4 A molecular sieve; camphor-10-sulfonic acid; mercury(II) cyanide; tetra-(n-butyl)ammonium iodide; mercury dibromide; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00032a601

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 123170-15-0
methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / (+/-)-camphorsulfonic acid / dimethylformamide / 3 h / Ambient temperature

2: 1) CaH₂, Bu₄NI, KOH / 1a) THF, DMSO, 0 deg C, 4h, 1b) RT, 16h, 2) ether

3: 83 percent / BH₃*NMe₃, AlCl₃, molecular sieve 4A / tetrahydrofuran / 1) 0 deg C, 0.5h, 2) RT, 2h

4: 64 percent / Hg(CN)2, HgBr₂, molecular sieve 4A / CCl₄ / 1) -20 deg C, 0.5h, 2) 0 deg C, 1h, 3) RT, 18h

With potassium hydroxide; aluminium trichloride; calcium hydride; trimethylamine-borane; 4 A molecular sieve; camphor-10-sulfonic acid; mercury(II) cyanide; tetra-(n-butyl)ammonium iodide; mercury dibromide; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00032a601