(1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol

Base Information

• Chemical Name: (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol
• CAS No.: 127685-46-5
• Molecular Formula: C₄₂H₆₈O₁₁Si₂
• Molecular Weight: 805.166
• Mol file: 127685-46-5.mol

Synonyms:(1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol

Chemical Property of (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol

There total 28 articles about (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol 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: 97.0%

(Z)-(1R,2S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-5-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-en-2-ol → (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol (127685-46-5) + (1R,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol (127685-46-5)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/ja00167a068

Reference yield: 97.0%

(Z)-(1R,2S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-5-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-en-2-ol → (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol (127685-46-5) + (1R,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol (127685-46-5)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/ja00167a068

Reference yield:

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol (127665-77-4) → (1S,2R)-1-{(2R,3S)-3-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(R)-oxiranyl-propyl]-oxiranyl}-2-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-2-(2-trimethylsilanyl-ethoxymethoxy)-ethanol (127685-46-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / L-diethyl tartrate (L-DET), Ti(O-iPr)4, t-BuOOH, 4-A sieves / CH₂Cl₂ / 20 h / -20 °C

2: 65 percent / toluene; hexane / Ambient temperature

3: 1.) TsCl, Et₃N, 2.) Triton B / 1.) CH₂Cl₂, 0 deg C, 24 h, 2.) methanol, RT, 2 h

4: 1.) n-butyllithium / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 20 min

5: 89 percent / H₂ / 20percent Pd/CaCO₃ / ethyl acetate / 8 h / Ambient temperature

6: 97 percent / m-chloroperbenzoic acid (m-CPBA), NaHCO₃ / CH₂Cl₂ / 10 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; N-benzyl-trimethylammonium hydroxide; sodium hydrogencarbonate; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In hexane; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja00167a068

upstream raw materials:

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol

(2S,3S)-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)-2-oxiranyl)methan-1-ol

tert-butyl(((S)-3-((R)-oxiran-2-yl)pent-4-yn-1-yl)oxy)diphenylsilane

(R)-[(2S,4S,5R)-2-Methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-(2-trimethylsilanyl-ethoxymethoxy)-acetaldehyde

Downstream raw materials:

C₄₁H₆₆O₁₀SSi₂

(2S,3R,4R,5S,8R,9S)-2-{(3R,4R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-thiophen-2-yl}-9-(2-methoxy-ethoxymethoxy)-8-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1,6-dioxa-spiro[4.5]decan-3-ol