(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

Base Information

Chemical Name:(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
CAS No.:1442422-67-4
Molecular Formula:C₄₂H₄₅NO₆S₂
Molecular Weight:723.954
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 33 articles about (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 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: 97.0%

: 1442422-57-2
(2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-4-O-6-S-(1-cyano)benzylidene-D-glycero-1,6-dithio-α-D-mannohepto-pyranoside

: 108-24-7
acetic anhydride

: 1442422-67-4
(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

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;
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)-1-thia-α-D-mannopyranoside

: 1442422-67-4
(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

Guidance literature:: Multi-step reaction with 12 steps

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

1.2: 2 h / -78 - 20 °C / Inert atmosphere

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

2.2: -78 - 20 °C / Inert atmosphere

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

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

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

5.2: 20 h / 20 °C / Inert atmosphere

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

6.2: 20 °C / Inert atmosphere

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

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

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

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

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

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

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; sodium hexamethyldisilazane; 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; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: |Swern Oxidation;
DOI:10.1016/j.tet.2013.04.094

Reference yield:

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

: 1442422-67-4
(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

Guidance literature:: Multi-step reaction with 8 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

With dmap; lithium aluminium tetrahydride; 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; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2013.04.094