(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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol

Base Information

• Chemical Name: (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol
• CAS No.: 127665-79-6
• Molecular Formula: C₄₂H₆₆O₁₀Si₂
• Molecular Weight: 787.151
• Mol file: 127665-79-6.mol

Synonyms:(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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol

Chemical Property of (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol

There total 11 articles about (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol 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:

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol (127665-77-4) → (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol (127665-79-6)

Guidance literature:

Multi-step reaction with 4 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; 4 A molecular sieve; N-benzyl-trimethylammonium hydroxide; triethylamine; p-toluenesulfonyl chloride; In hexane; dichloromethane; toluene;

DOI:10.1021/ja00167a068

Reference yield:

(2S,3S)-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)-2-oxiranyl)methan-1-ol (116003-84-0) → (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol (127665-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / toluene; hexane / Ambient temperature

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

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

With n-butyllithium; N-benzyl-trimethylammonium hydroxide; triethylamine; p-toluenesulfonyl chloride; In hexane; toluene;

DOI:10.1021/ja00167a068

Reference yield:

(2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol (127685-45-4) → (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-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol (127665-79-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 6 h / Heating

3: 1.) KH / 1.) THF, 0 deg C, 1 h, 2.) RT, 1 h

4: 98 percent / n-Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

5: 1.) N-bromosuccinimide, collidine, 2.) TsOH / 1.) MeCN, RT, 10 min, 2.) 0 deg C, 5 min

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) RT, 90 min

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

With 1H-imidazole; 2,3,5-trimethyl-pyridine; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; iodine; potassium hydride; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00167a068

upstream raw materials:

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

(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

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

(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

(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