2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate
CAS No.:257933-05-4
Molecular Formula:C₇₂H₉₃NO₂₅Si
Molecular Weight:1400.61
Hs Code.:

2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

Synonyms:2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

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Chemical Property of 2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

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Technology Process of 2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

There total 6 articles about 2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate 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: 65.0%

: 142602-45-7
2-(trimethylsilyl)ethyl α-(dimethoxyphosphoryl)-N-(tert-butyloxycarbonyl)glycinate

: 257933-04-3
acetic acid 3-acetoxy-6-acetoxymethyl-2-[4,5-diacetoxy-2-acetoxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-5-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

: 257933-05-4
2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

Guidance literature:: With N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; at -78 ℃; for 4h;
DOI:10.1021/jo991096m

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 257933-05-4
2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / 4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 15 h / 0 - 25 °C

2: PCl₃ / toluene / 15 h / 70 °C

3: 3.826 g / toluene / 2 h

4: 98 percent / H₂ / Pd/C / methanol / 15 h / 4654.33 Torr

5: 65 percent / TMG / tetrahydrofuran / 4 h / -78 °C

With dmap; hydrogen; dicyclohexyl-carbodiimide; phosphorus trichloride; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Esterification / 2: Substitution / 3: phosphorylation / 4: Hydrogenolysis / 5: Horner-Emmons olefination;
DOI:10.1021/jo991096m

Reference yield:

: 134038-88-3
2-(trimethylsilyl)ethyl α-(dimethoxyphosphoryl)-N-(benzyloxycarbonyl)glycinate

: 257933-05-4
2-(trimethylsilyl)ethyl 4-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2-(tert-butyloxycarbonylamino)-2-butenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / H₂ / Pd/C / methanol / 15 h / 4654.33 Torr

2: 65 percent / TMG / tetrahydrofuran / 4 h / -78 °C

With hydrogen; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Hydrogenolysis / 2: Horner-Emmons olefination;
DOI:10.1021/jo991096m