methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

Base Information

Chemical Name:methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate
CAS No.:1453169-69-1
Molecular Formula:C₂₉H₃₇NO₁₃S
Molecular Weight:639.678
Hs Code.:

Synonyms:methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

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Chemical Property of methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

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Technology Process of methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

There total 1 articles about methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)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: 100.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1235555-29-9
methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 1453169-69-1
methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: With dmap; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201300664

Reference yield:

: 1453169-69-1
methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: methyl (5-tert-butyloxycabonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 5 h / 0 °C / Molecular sieve; Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere; Molecular sieve

3: camphor-10-sulfonic acid / methanol / 16 h / 20 °C / Inert atmosphere

With N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; In methanol; dichloromethane;
DOI:10.1002/ejoc.201300664

Reference yield:

: 1453169-69-1
methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 381716-71-8
(5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 5 h / 0 °C / Molecular sieve; Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere; Molecular sieve

3: camphor-10-sulfonic acid / methanol / 16 h / 20 °C / Inert atmosphere

4: potassium tert-butylate / tetrahydrofuran; methanol / 16 h / 20 °C / Inert atmosphere

5: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

6: triethylamine / methanol / 5 h / 0 °C / Inert atmosphere

With N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; potassium tert-butylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/ejoc.201300664