1-((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-propene

Base Information

Chemical Name:1-((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-propene
CAS No.:257933-03-2
Molecular Formula:C₆₁H₇₂O₂₁
Molecular Weight:1141.23
Hs Code.:

Synonyms:1-((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-propene

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Chemical Property of 1-((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-propene

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Technology Process of 1-((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-propene

There total 1 articles about 1-((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-propene 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: 93.0%

: 108-24-7
acetic anhydride

: 1-((2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(β-D-galactopyranosyl)-(1->4)-α-D-glucopyranosyl)-2-propene

: 257933-03-2
1-((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-propene

Guidance literature:: With pyridine; dmap; for 15h;
DOI:10.1021/jo991096m

Reference yield: 75.0%

: 257933-03-2
1-((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-propene

: 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

Guidance literature:: 1-((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-propene; With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 25 ℃; for 15h;
DOI:10.1021/jo991096m

Reference yield:

: 257933-03-2
1-((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-propene

: 2-(trimethylsilyl)ethyl (2S)-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)butanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

1.2: 75 percent / Me₂S / CH₂Cl₂; methanol / 15 h / -78 - 25 °C

2.1: 65 percent / TMG / tetrahydrofuran / 4 h / -78 °C

3.1: 98 percent / H₂ / [(COD)Rh-((S,S)-Et-DuPHOS)]OTf / tetrahydrofuran / 48 h / 25 °C / 4654.33 Torr

With hydrogen; sodium hydrogencarbonate; ozone; N,N,N',N'-tetramethylguanidine; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; 1.1: ozonolysis / 1.2: Reduction / 2.1: Horner-Emmons olefination / 3.1: Catalytic hydrogenation;
DOI:10.1021/jo991096m