(R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester

Base Information

• Chemical Name: (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester
• CAS No.: 393589-27-0
• Molecular Formula: C₄₂H₆₉NO₈
• Molecular Weight: 716.012
• Mol file: 393589-27-0.mol

Synonyms:(R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester

Chemical Property of (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester

There total 8 articles about (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester 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: 95.0%

2-(5-{2-(tert-butyl-dimethyl-silanyloxy)-3-[5-(2-dimethylamino-pentyl)-tetrahydro-furan-2-yl]-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid 1-[5-(1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester (393589-26-9) → (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester (393589-27-0)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 25 ℃;

DOI:10.1016/S0040-4039(01)01665-3

Reference yield:

2-(5-<3-<5-(2-dimethylamino-pentyl)tetrahydro-furan-2-yl>-2-hydroxy-1-methyl-butyl>tetrahydro-furan-2-yl)propionic acid methyl ester (158355-82-9) → (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester (393589-27-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 25 °C

2: 81 percent / LiOH / tetrahydrofuran; methanol / 25 °C

3: Et₃N / tetrahydrofuran / 25 °C

4: 88 percent / DMAP / toluene / 25 °C

5: 95 percent / aq. HF / acetonitrile / 25 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; hydrogen fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)01665-3

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (R)-2-((2R,5S)-5-{(1S,2S,3S)-3-[(2R,5S)-5-((R)-2-Dimethylamino-pentyl)-tetrahydro-furan-2-yl]-2-hydroxy-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid (S)-1-[(2S,5R)-5-((S)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester (393589-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / BnOLi / tetrahydrofuran / 25 °C

2: 88 percent / DMAP / toluene / 25 °C

3: 95 percent / aq. HF / acetonitrile / 25 °C

With dmap; hydrogen fluoride; lithium benzyloxide; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)01665-3

upstream raw materials:

2-(5-{2-(tert-butyl-dimethyl-silanyloxy)-3-[5-(2-dimethylamino-pentyl)-tetrahydro-furan-2-yl]-1-methyl-butyl}-tetrahydro-furan-2-yl)-propionic acid 1-[5-(1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-ylmethyl]-butyl ester

2-(5-<3-<5-(2-dimethylamino-pentyl)tetrahydro-furan-2-yl>-2-hydroxy-1-methyl-butyl>tetrahydro-furan-2-yl)propionic acid methyl ester

benzyl alcohol

(1S,2S,5S,7R)-2-Methyl-5-propyl-4,10-dioxa-bicyclo[5.2.1]decan-3-one

Downstream raw materials:

pamamycin-607