methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Base Information

Chemical Name:methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate
CAS No.:402948-44-1
Molecular Formula:C₂₈H₃₄Cl₃NO₁₄
Molecular Weight:714.935
Hs Code.:

Synonyms:methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

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Chemical Property of methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

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Technology Process of methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

There total 4 articles about methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]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: 66.0%

: 100-51-6,185532-71-2
benzyl alcohol

: 402948-43-0
methyl (phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate

: methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid]onate

: 402948-44-1
methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; at -25 ℃; for 1h;
DOI:10.1021/jo015930v

Reference yield:

: 118977-25-6
methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

: 402948-44-1
methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Guidance literature:: Multi-step reaction with 4 steps

1: MsOH / methanol / 24 h / 65 °C

2: 10.86 g / aq. NaHCO₃ / dioxane / 1 h

3: 94 percent / pyridine / 24 h / 20 °C

4: 66 percent / NIS; TfOH / acetonitrile / 1 h / -25 °C

With pyridine; N-iodo-succinimide; methanesulfonic acid; trifluorormethanesulfonic acid; sodium hydrogencarbonate; In 1,4-dioxane; methanol; acetonitrile;
DOI:10.1021/jo015930v

Reference yield:

: 367922-37-0
(2R,4S,5R,6R)-5-Amino-4-hydroxy-2-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 402948-44-1
methyl [benzyl 5-(2,2,2-trichloroethoxycarbonylamino)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Guidance literature:: Multi-step reaction with 3 steps

1: 10.86 g / aq. NaHCO₃ / dioxane / 1 h

2: 94 percent / pyridine / 24 h / 20 °C

3: 66 percent / NIS; TfOH / acetonitrile / 1 h / -25 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydrogencarbonate; In 1,4-dioxane; acetonitrile;
DOI:10.1021/jo015930v