(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

Base Information

• Chemical Name: (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
• CAS No.: 127665-80-9
• Molecular Formula: C₄₁H₆₆O₁₀SSi₂
• Molecular Weight: 807.206
• Mol file: 127665-80-9.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 32 articles about (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 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) → C41H66O10SSi2 (127665-80-9,127758-13-8)

Guidance literature:

Multi-step reaction with 8 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

7: 88 percent / 20percent NaSH*xH₂O / ethanol / 2 h / Ambient temperature

8: TsOH / CH₂Cl₂ / 1 h / -20 °C

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

DOI:10.1021/ja00167a068

Reference yield:

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol (127665-77-4) → (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 (127665-80-9,127758-13-8)

Guidance literature:

Multi-step reaction with 8 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

7: 88 percent / 20percent NaSH*xH₂O / ethanol / 2 h / Ambient temperature

8: TsOH / CH₂Cl₂ / 1 h / -20 °C

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

DOI:10.1021/ja00167a068

Reference yield:

tert-butyl(((S)-3-((R)-oxiran-2-yl)pent-4-yn-1-yl)oxy)diphenylsilane (127665-78-5) → C41H66O10SSi2 (127665-80-9,127758-13-8)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 89 percent / H₂ / 20percent Pd/CaCO₃ / ethyl acetate / 8 h / Ambient temperature

3: 97 percent / m-chloroperbenzoic acid (m-CPBA), NaHCO₃ / CH₂Cl₂ / 10 h / Ambient temperature

4: 88 percent / 20percent NaSH*xH₂O / ethanol / 2 h / Ambient temperature

5: TsOH / CH₂Cl₂ / 1 h / -20 °C

With sodium hydrogensulfide; n-butyllithium; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In ethanol; dichloromethane; ethyl acetate;

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