ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside
CAS No.:1240564-06-0
Molecular Formula:C₂₆H₃₄O₆S
Molecular Weight:474.618
Hs Code.:

Synonyms:ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

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Chemical Property of ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

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Technology Process of ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

There total 5 articles about ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside 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: 66.0%

: ethyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-D-glycero-D-manno-heptpyranoside

: 100-39-0
benzyl bromide

: 1240564-06-0
ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

Guidance literature:: ethyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-D-glycero-D-manno-heptpyranoside; With di(n-butyl)tin oxide; In toluene; for 4h; Reflux; Inert atmosphere;

benzyl bromide; In acetonitrile; at 70 ℃; for 10h; Inert atmosphere;
DOI:10.1002/anie.202004267

Reference yield:

: ethyl 4-O-benzyl-6,7-dideoxy-2,3-O-isopropylidene-1-thio-α-D-glycero-D-manno-hept-6-enopyranoside

: 1240564-06-0
ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexacyanoferrate(III); potassium osmate(VI) dihydrate; potassium carbonate / tert-butyl alcohol; water; toluene / 36 h / 0 °C / Inert atmosphere

2.1: di(n-butyl)tin oxide / toluene / 4 h / Reflux; Inert atmosphere

2.2: 10 h / 70 °C / Inert atmosphere

With potassium osmate(VI) dihydrate; di(n-butyl)tin oxide; potassium carbonate; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol;
DOI:10.1002/anie.202004267

Reference yield:

: 195192-35-9
ethyl 4-O-benzyl-2,3-O-isoproylidene-1-thio-α-D-mannopyranoside

: 1240564-06-0
ethyl 4,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-D-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 12 h / -78 - 20 °C / Inert atmosphere

3.1: potassium hexacyanoferrate(III); potassium osmate(VI) dihydrate; potassium carbonate / tert-butyl alcohol; water; toluene / 36 h / 0 °C / Inert atmosphere

4.1: di(n-butyl)tin oxide / toluene / 4 h / Reflux; Inert atmosphere

4.2: 10 h / 70 °C / Inert atmosphere

With potassium osmate(VI) dihydrate; n-butyllithium; oxalyl dichloride; di(n-butyl)tin oxide; potassium carbonate; dimethyl sulfoxide; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1002/anie.202004267