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

Base Information

• Chemical Name: (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-acetylene
• CAS No.: 1301629-44-6
• Molecular Formula: C₅₁H₅₄O₁₀
• Molecular Weight: 826.984
• Mol file: 1301629-44-6.mol

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

Chemical Property of (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-acetylene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-acetylene

There total 8 articles about (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-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:

(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-butyl)-acetylene (1221720-06-4) → (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-acetylene (1301629-44-6)

Guidance literature:

(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-butyl)-acetylene; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

1-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-trimethylsilylacetylene)-D-ribo-butan-1-ol (1221720-02-0) → (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-acetylene (1301629-44-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

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

2.2: 1 h / 0 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

4.1: ammonium fluoride / methanol / 3 h / Reflux

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

5.2: 1.5 h / -78 - 20 °C

With 1H-imidazole; ammonium fluoride; n-butyllithium; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5.2: Swern oxidation;

DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

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-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-5'-carbaldehyde)-acetylene (1301629-44-6)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 1 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

3.1: ammonium fluoride / methanol / 3 h / Reflux

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

4.2: 1.5 h / -78 - 20 °C

With ammonium fluoride; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.2: Swern oxidation;

DOI:10.1016/j.bmcl.2011.02.044

upstream raw materials:

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

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

(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

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-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

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