methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside
CAS No.:1442422-70-9
Molecular Formula:C₅₀H₅₃NO₁₀S
Molecular Weight:860.038
Hs Code.:

methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

Synonyms:methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

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Chemical Property of methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

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Technology Process of methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

There total 17 articles about methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside 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: 78.0%

: 1442422-66-3
(2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1,6-dithio-α-D-mannoheptopyranoside

: 14133-63-2
methyl 2,3-O-isopropylidene-α-L-rhamnoside

: 1442422-70-9
methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: (2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1,6-dithio-α-D-mannoheptopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -50 ℃; for 1h; Inert atmosphere;

methyl 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -50 ℃; for 8h; Inert atmosphere;
DOI:10.1016/j.tet.2013.04.094

Reference yield:

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

: 1442422-70-9
methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 12 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: trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine / dichloromethane / 1 h / -50 °C / Inert atmosphere

12.2: 8 h / -50 °C / Inert atmosphere

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 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; trifluoroacetic acid; 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:

: 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

: 1442422-70-9
methyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside-(1→4)-2,3-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 7 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: trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine / dichloromethane / 1 h / -50 °C / Inert atmosphere

7.2: 8 h / -50 °C / Inert atmosphere

With lithium aluminium tetrahydride; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 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; trifluoroacetic acid; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2013.04.094