ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside
CAS No.:173725-83-2
Molecular Formula:C₃₃H₃₈O₈S
Molecular Weight:594.726
Hs Code.:

Synonyms:ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

There total 1 articles about ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-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: 99.0%

: 108-30-5
succinic acid anhydride

: 129750-23-8
Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 173725-83-2
ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

Guidance literature:: With dmap; In pyridine; at 25 ℃; for 24h;
DOI:10.1016/0040-4039(95)01952-E

Reference yield: 60.0%

: 173725-83-2
ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

: benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside

: 173725-84-3
benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[4-(ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-2-O-yl)-1,4-dioxobutyl]-α-D-glucopyranoside

Guidance literature:: With dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 6h;
DOI:10.1016/0040-4039(95)01952-E

Reference yield:

: 173725-83-2
ethyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside

: 173725-86-5
benzyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside 2',3-succinate

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / DCC; DMAP; 1-hydroxy-1H-benzotriazole / CH₂Cl₂ / 24 h / 20 °C

2: 88 percent / NaCNBH₃; 3 Angstroem molecular sieves; HCl / tetrahydrofuran; diethyl ether / 20 °C

3: 54 percent / 3 Angstroem mol. sieves; NIS; Me₃SiOTf / acetonitrile / 0.08 h / -30 °C

With hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium cyanoborohydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 1: Acylation / 2: Ring cleavage / 3: Cyclization;
DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U