Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

Base Information

Chemical Name:Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate
CAS No.:162613-20-9
Molecular Formula:C₂₈H₃₆O₇S
Molecular Weight:516.656
Hs Code.:

Synonyms:Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

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Chemical Property of Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

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Technology Process of Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

There total 6 articles about Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate 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: 85.0%

: 3282-30-2
pivaloyl chloride

: 162613-17-4
Methyl (ethyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranosid)uronate

: 162613-20-9
Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

Guidance literature:: With pyridine; at 65 ℃; for 144h;
DOI:10.1021/jo00112a046

Reference yield:

: 141810-60-8
ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 162613-20-9
Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / pyridine / 2 h

2: 68 percent / AlCl₃, BH₃-Me₃N, 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

3: pyridine, TFA, DCC / dimethylsulfoxide / Ambient temperature

4: PDC / dimethylformamide / Ambient temperature

5: 70 percent / MeONa / methanol / 24 h

6: 85 percent / pyridine / 144 h / 65 °C

With pyridine; dipyridinium dichromate; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium methylate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00112a046

Reference yield:

: 162681-47-2
ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 162613-20-9
Methyl (ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranosid)uronate

Guidance literature:: Multi-step reaction with 5 steps

1: 68 percent / AlCl₃, BH₃-Me₃N, 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

2: pyridine, TFA, DCC / dimethylsulfoxide / Ambient temperature

3: PDC / dimethylformamide / Ambient temperature

4: 70 percent / MeONa / methanol / 24 h

5: 85 percent / pyridine / 144 h / 65 °C

With pyridine; dipyridinium dichromate; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium methylate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00112a046