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

Base Information

• Chemical Name: 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
• CAS No.: 1442422-68-5
• Molecular Formula: C₄₁H₄₉NO₉S
• Molecular Weight: 731.907
• Mol file: 1442422-68-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 33 articles about 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 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: 96.0%

(2-methyl-5-tert-butylphenyl) 3-O-acetyl-2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-D-glycero-1,6-dithio-α-D-mannoheptopyranoside (1442422-67-4) + tert-butyl 6-hydroxyhexanoate (73839-20-0) → 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:

(2-methyl-5-tert-butylphenyl) 3-O-acetyl-2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-D-glycero-1,6-dithio-α-D-mannoheptopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

tert-butyl 6-hydroxyhexanoate; In dichloromethane; at -78 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2013.04.094

Reference yield:

(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-1-thia-α-D-mannopyranoside (1442422-75-4) → 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 14 steps

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

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

2.2: 2 h / -78 - 20 °C / Inert atmosphere

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

3.2: -78 - 20 °C / Inert atmosphere

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

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

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

6.2: 20 h / 20 °C / Inert atmosphere

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

7.2: 20 °C / Inert atmosphere

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

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

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

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

12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

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

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

14.2: 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 hexamethyldisilazane; diisobutylaluminium hydride; di(n-butyl)tin oxide; 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; hexane; dichloromethane; water; toluene; 2.1: |Swern Oxidation;

DOI:10.1016/j.tet.2013.04.094

Reference yield:

(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranoside (1442422-62-9) → 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 9 steps

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

1.2: 20 h / 20 °C / Inert atmosphere

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

2.2: 20 °C / Inert atmosphere

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

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

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

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

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

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

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

9.2: 2 h / -78 - 20 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; sodium hexamethyldisilazane; di(n-butyl)tin oxide; 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; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1016/j.tet.2013.04.094

upstream raw materials:

(2-methyl-5-tert-butylphenyl) 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-D-glycero-1-thia-α-D-mannoheptopyranoside

(2-methyl-5-tert-butylphenyl) 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-1-thia-α-D-mannoheptopyranoside

(2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2'-3'-diyl)-L-glycero-1-thia-α-D-mannoheptopyranoside

(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

Refernces