{2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane
• CAS No.: 215120-29-9
• Molecular Formula: C₂₇H₄₈O₄S₂Si
• Molecular Weight: 528.893
• Mol file: 215120-29-9.mol

Synonyms:{2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Chemical Property of {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

There total 7 articles about {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane 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: 93.0%

{2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2,2-bis-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (215120-32-4) → {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (215120-29-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -60 ℃;

DOI:10.1021/ja982431b

Reference yield:

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (162718-31-2) → {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (215120-29-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

2: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

3: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

4: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / dimethylformamide / 0 °C

7: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc(II) iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja982431b

Reference yield:

[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (215120-31-3) → {2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2-ethanesulfinyl-2-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (215120-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: imidazole / dimethylformamide / 0 °C

4: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

With 1H-imidazole; lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja982431b

upstream raw materials:

{2-[(2S,3R,4S,6S)-4-Benzyloxy-6-(2,2-bis-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

[(2S,3R,4S,6S)-4-Benzyloxy-6-((E)-2-methoxy-vinyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Downstream raw materials:

(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

((2S,3R,4S,6S)-4-Benzyloxy-6-{(2R,4R,6R)-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl}-3-methyl-tetrahydro-pyran-2-yl)-acetaldehyde

{(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid