(2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol

Base Information

• Chemical Name: (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol
• CAS No.: 223564-85-0
• Molecular Formula: C₃₉H₆₀O₆Si
• Molecular Weight: 652.987
• Mol file: 223564-85-0.mol

Synonyms:(2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol

Chemical Property of (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol

There total 11 articles about (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol 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: 40.0%

methanol (67-56-1) + (3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-[(R)-6-((R)-4-ethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-4-trimethylsilanyloxy-hex-1-ynyl]-3,5-dimethyl-tetrahydro-pyran-2-ol → (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol (223564-85-0)

Guidance literature:

With Amberlite;

DOI:10.1055/s-1999-2607

Reference yield:

(2'R,4S,5R)-(-)-3-(2'-Methyl-4'-ethyl-1'-oxopent-4'-enyl)-4-methyl-5-phenyloxazolidin-2-one (223564-49-6) → (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol (223564-85-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 77 percent / aq. K₃Fe(CN)6; K₂OsO₄*H₂O; (DHQ)2PHAL / 2-methyl-propan-2-ol / 0.5 h / 0 °C

2.1: 63 percent / LiBH₄ / diethyl ether / 1 h

3.1: 75 percent / p-TsOH / 1 h / 20 °C

4.1: 76 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

5.1: Mg; I₂; HgCl₂ / diethyl ether

5.2: 83 percent / diethyl ether / 0.5 h / 20 °C

6.1: 87 percent / CH₂Cl₂ / 1 h

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

8.1: Amberlite resin IR 118

With potassium osmate(VI); lithium borohydride; n-butyllithium; tetrapropylammonium perruthennate; Hydroquinone 1,4-phthalazinediyl diether; 4 A molecular sieve; Amberlite resin IR 118; iodine; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; mercury dichloride; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1039/b008159k

Reference yield:

2-(Iodomethyl)but-1-ene (66702-94-1) → (2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol (223564-85-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 55 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

2.1: 77 percent / aq. K₃Fe(CN)6; K₂OsO₄*H₂O; (DHQ)2PHAL / 2-methyl-propan-2-ol / 0.5 h / 0 °C

3.1: 63 percent / LiBH₄ / diethyl ether / 1 h

4.1: 75 percent / p-TsOH / 1 h / 20 °C

5.1: 76 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

6.1: Mg; I₂; HgCl₂ / diethyl ether

6.2: 83 percent / diethyl ether / 0.5 h / 20 °C

7.1: 87 percent / CH₂Cl₂ / 1 h

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

9.1: Amberlite resin IR 118

With potassium osmate(VI); lithium borohydride; n-butyllithium; tetrapropylammonium perruthennate; Hydroquinone 1,4-phthalazinediyl diether; 4 A molecular sieve; Amberlite resin IR 118; iodine; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; mercury dichloride; potassium hexacyanoferrate(III); lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1039/b008159k

upstream raw materials:

methanol

2-(chloromethyl)-1-butene

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one

2-(Iodomethyl)but-1-ene

Downstream raw materials:

(2R,4R,5S/R,2'S/R,3'R,5'S,6'S,1''S)-8-{6-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-methoxy-3,5-dimethyltetrahydro-2H-pyran-2-yl}-2-ethyl-2,5-dihydroxy-4-methyloct-7-yn-1-yl acetate

(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methanal

(2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene