(2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Base Information

• Chemical Name: (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene
• CAS No.: 1221720-04-2
• Molecular Formula: C₅₀H₆₄O₁₀Si
• Molecular Weight: 853.138
• Mol file: 1221720-04-2.mol

Synonyms:(2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Chemical Property of (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

There total 5 articles about (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene 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:

5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose (876935-54-5) + 2-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-03-1) → (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-04-2)

Guidance literature:

2-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene; With n-butyllithium; In diethyl ether; at -78 - 0 ℃;

With zinc(II) chloride; In diethyl ether; at 0 ℃; for 1h;

5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose; Further stages;

DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

2,3-O-isopropylidene-1-trimethylsilylacetylene-D-ribo-butan-1,4-diol (174591-00-5) → (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-04-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

2.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

3.1: n-butyllithium / diethyl ether / -78 - 0 °C

3.2: 1 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

2,3-O-isopropylidene-D-erythrose (189996-60-9) → (2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-04-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / -78 - 6 °C

2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

3.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

4.1: n-butyllithium / diethyl ether / -78 - 0 °C

4.2: 1 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.02.044

upstream raw materials:

5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose

2-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

2,3-O-isopropylidene-1-trimethylsilylacetylene-D-ribo-butan-1,4-diol

1-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-trimethylsilylacetylene)-D-ribo-butan-1-ol

Downstream raw materials:

(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadec-5',6'-enyl)-acetylene

(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadecyl)-ethane

(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

(2'S,3'R,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-hexacosanoyl-D-ribo-heptadecyl)-ethane