(2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside

Base Information

• Chemical Name: (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside
• CAS No.: 1379519-57-9
• Molecular Formula: C₂₅H₃₄O₉S
• Molecular Weight: 510.606
• Mol file: 1379519-57-9.mol

Synonyms:(2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside

Chemical Property of (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside

There total 1 articles about (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside 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: 93.0%

2-methyl-5-tert-butylthiophenol (7340-90-1) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside (1379519-57-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.04.094

Reference yield: 100.0%

(2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside (1379519-57-9) → (2-methyl-5-tert-butylphenyl) 1-thio-α-D-mannopyranoside (1361016-58-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.04.094

Reference yield:

(2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside (1379519-57-9) → 5-tert-butyloxycarbonylpentyl 3-O-acetyl-2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-D-glycero-1-thia-α-D-mannoheptopyranoside (1442422-68-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: sodium methylate / methanol / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 60 °C / Inert atmosphere

3.1: di(n-butyl)tin oxide / toluene / Inert atmosphere; Reflux

3.2: 20 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 - 20 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide / tetrahydrofuran / 2 h / -60 - -40 °C / Inert atmosphere

6.2: 2 h / -78 - 20 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere

7.2: -78 - 20 °C / Inert atmosphere

8.1: copper(II) oxide; copper dichloride / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

9.1: lithium aluminium tetrahydride / tetrahydrofuran / 4.17 h / -78 °C / Inert atmosphere

10.1: di(n-butyl)tin oxide / toluene / Inert atmosphere; Reflux

10.2: 20 h / 20 °C / Inert atmosphere

11.1: sodium hexamethyldisilazane; N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide / tetrahydrofuran / 0.2 h / -78 °C / Inert atmosphere

11.2: 20 °C / Inert atmosphere

12.1: trifluoroacetic acid; water / dichloromethane / 3 h / -35 - -25 °C / Inert atmosphere

13.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -78 - 20 °C / Inert atmosphere

14.1: camphor-10-sulfonic acid / dichloromethane / 20 °C / Inert atmosphere

15.1: boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

16.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

17.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

18.1: trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 1,1'-sulfinylbisbenzene / dichloromethane / 1 h / -78 °C / Inert atmosphere

18.2: 2 h / -78 - 20 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; sodium methylate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; copper dichloride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6.1: |Swern Oxidation;

DOI:10.1016/j.tet.2013.04.094

upstream raw materials:

2-methyl-5-tert-butylthiophenol

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

C₃₂H₄₄O₇S

C₃₂H₄₄O₇S

(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenyl-methyl)-7-S-tris(thiophenol)-l-glycero-1-thia-α-D-thiomannoheptopyranoside

S-phenyl [(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranosylurinate]

Refernces