Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid

Base Information

• Chemical Name: Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid
• CAS No.: 74995-92-9
• Molecular Formula: C₁₇H₂₅NO₇S
• Molecular Weight: 387.454
• Mol file: 74995-92-9.mol

Synonyms:Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid

Chemical Property of Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid

There total 12 articles about Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid 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: 40.0%

Methyl-2-O-acetyl-3,4,6-tridesoxy-3-C-methyl-α-D-threo-hex-3-enopyranosid (74995-91-8) + chloramine T trihydrate → Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid (74995-92-9)

Guidance literature:

With osmium(VIII) oxide; In tert-butyl alcohol; at 60 ℃;

DOI:10.1016/S0040-4039(01)85568-4

Reference yield:

methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside (74995-84-9) → Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid (74995-92-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / Et₃N, H₂ / Raney-Ni / methanol / 2942.03 Torr

2: 85 percent / SOCl₂ / benzene; pyridine / 3 h / 5 °C

3: 98 percent / 2 N NaOH / ethanol / 15 h / Ambient temperature

4: 73 percent / tri-n-butylphosphane / benzene / 3 h

5: 77 percent / 85percent 3-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 - 5 °C

6: 75 percent / pyridine / 5 h / 70 °C

7: 1) OsO₄, 2) NaHSO₃ / 1) tert-BuOH, 7 d, 60 deg C, 2) tert-BuOH, 3 h, 60 deg C

With sodium hydroxide; osmium(VIII) oxide; thionyl chloride; tributylphosphine; hydrogen; sodium hydrogensulfite; triethylamine; 3-chloro-benzenecarboperoxoic acid; nickel; In pyridine; methanol; ethanol; dichloromethane; benzene;

Reference yield:

Methyl-4,6-O-benzyliden-2-desoxy-3-C-methyl-α-D-ribo-hexopyranosid (6752-52-9,13264-07-8,18424-64-1,19231-32-4,77481-74-4,77481-75-5,77481-76-6,77481-77-7,78086-67-6,100100-70-7) → Methyl-2-O-acetyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid (74995-92-9)

Guidance literature:

Multi-step reaction with 8 steps

1: N-bromosuccinimide, BaCO₃ / CCl₄ / 2 h / Heating

2: 83 percent / Et₃N, H₂ / Raney-Ni / methanol / 2942.03 Torr

3: 85 percent / SOCl₂ / benzene; pyridine / 3 h / 5 °C

4: 98 percent / 2 N NaOH / ethanol / 15 h / Ambient temperature

5: 73 percent / tri-n-butylphosphane / benzene / 3 h

6: 77 percent / 85percent 3-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 - 5 °C

7: 75 percent / pyridine / 5 h / 70 °C

8: 1) OsO₄, 2) NaHSO₃ / 1) tert-BuOH, 7 d, 60 deg C, 2) tert-BuOH, 3 h, 60 deg C

With sodium hydroxide; N-Bromosuccinimide; osmium(VIII) oxide; thionyl chloride; tributylphosphine; hydrogen; sodium hydrogensulfite; triethylamine; 3-chloro-benzenecarboperoxoic acid; barium carbonate; nickel; In pyridine; methanol; tetrachloromethane; ethanol; dichloromethane; benzene;

upstream raw materials:

chloroamine-T

Methyl-2-O-acetyl-3,4,6-tridesoxy-3-C-methyl-α-D-threo-hex-3-enopyranosid

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

Methyl-4,6-O-benzyliden-2-desoxy-3-C-methyl-α-D-ribo-hexopyranosid

Downstream raw materials:

Methyl-4,6-didesoxy-3-C-methyl-N-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid

Methyl-4,6-didesoxy-3-C-methyl-4-(p-tolylsulfonylamino)-α-D-altropyranosid