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

Base Information

• Chemical Name: 2-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene
• CAS No.: 1221720-03-1
• Molecular Formula: C₂₃H₃₆O₅Si
• Molecular Weight: 420.621
• Mol file: 1221720-03-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-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: 80.0%

1-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-trimethylsilylacetylene)-D-ribo-butan-1-ol (1221720-02-0) + p-Methoxybenzyl bromide (2746-25-0) → 2-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-03-1)

Guidance literature:

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃; regioselective reaction;

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-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-03-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

With 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; 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-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene (1221720-03-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / -78 - 6 °C

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

3: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

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

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

p-Methoxybenzyl bromide

2,3-O-isopropylidene-D-erythrose

Downstream raw materials:

(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

(2'S,3'S,4'S)-1-(5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-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-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