(S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one
• CAS No.: 196080-31-6
• Molecular Formula: C₄₀H₆₇NO₈Si₂
• Molecular Weight: 746.145
• Mol file: 196080-31-6.mol

Synonyms:(S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one

There total 17 articles about (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one 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: 83.0%

(S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-pent-1-ene (196080-24-7) + (S)-4-Benzyl-3-{3-[(2R,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-propionyl}-oxazolidin-2-one (196080-23-6) → (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one (196080-31-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -20 ℃;

DOI:10.1016/S0040-4039(97)01336-1

Reference yield:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one (196080-31-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / 1.) O₃, 2.) NaBH₄ / methanol / -78 °C

2: 99 percent / iPr₂NEt / CH₂Cl₂

3: 95 percent / TBAF / tetrahydrofuran

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂

5: 53 percent / NaH / tetrahydrofuran / 0 °C

6: 75 percent / H₂ / (PPh₃)3RhCl / ethyl acetate

7: 99 percent / p-TsOH / methanol

8: 1.) (Imid)2C=S, 2.) P(OEt)3 / 1.) toluene, reflux, 2.) reflux

9: 83 percent / LDA / tetrahydrofuran / -78 - -20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; lithium diisopropyl amide; triethyl phosphite; Wilkinson's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(97)01336-1

Reference yield:

[(3aR,4R,6S,7aS)-4-(2-Methoxymethoxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-methanol (196080-38-3) → (S)-4-Benzyl-3-{(2S,6S)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl]-4-methylene-heptanoyl}-oxazolidin-2-one (196080-31-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / Dess-Martin periodinane / CH₂Cl₂

2: 53 percent / NaH / tetrahydrofuran / 0 °C

3: 75 percent / H₂ / (PPh₃)3RhCl / ethyl acetate

4: 99 percent / p-TsOH / methanol

5: 1.) (Imid)2C=S, 2.) P(OEt)3 / 1.) toluene, reflux, 2.) reflux

6: 83 percent / LDA / tetrahydrofuran / -78 - -20 °C

With hydrogen; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,1'-Thiocarbonyldiimidazole; lithium diisopropyl amide; triethyl phosphite; Wilkinson's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(97)01336-1

upstream raw materials:

(S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-pent-1-ene

(S)-4-Benzyl-3-{3-[(2R,6R)-6-(2-methoxymethoxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-propionyl}-oxazolidin-2-one

(S)-dimethyl 2-hydroxypentanedioate

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol