ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

Base Information

Chemical Name:ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate
CAS No.:112138-78-0
Molecular Formula:C₂₅H₃₄O₆
Molecular Weight:430.541
Hs Code.:

Synonyms:ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

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Chemical Property of ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

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Technology Process of ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

There total 18 articles about ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate 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:

: 78686-47-2
1,5-anhydro-2-deoxy-3-O-propanoyl-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-gluco-hex-1-enitol

: 112138-78-0
ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

Guidance literature:: Multi-step reaction with 18 steps

1: 98 percent / tetra-N-butyl-ammonium fluoride trihydrate / tetrahydrofuran / 1 h / 0 °C

2: 90 percent / pyridine / Ambient temperature

3: 87 percent / sodium iodide / butan-2-one / 4 h / 80 °C

4: 99 percent / diazabicycloundecene / benzene / 1 h / 84 °C

6: 70 percent / p-toluenesulfonic acid / Ambient temperature

7: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

8: 1) oxalyl chloride, dimethyl sulfoxide, (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, RT, overnight

9: 96 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

10: 97 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / Ambient temperature

11: 97 percent / p,p'-di-tert-butylbiphenyl, Li / tetrahydrofuran / -78 °C

12: 93 percent / oxalyl chloride, dimethyl sulfoxide, (i-Pr)2NEt / CH₂Cl₂ / -78 °C

13: 89 percent / n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

14: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

15: 90 percent / (+)-diisopropyltartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH₂Cl₂ / 5 h / -20 °C

16: copper bromide-dimethyl sulfide complex / diethyl ether / 4 h / 0 °C

17: p-toluenesulfonic acid / CHCl₃ / 0.5 h / Ambient temperature

18: 1) pyridinium chlorochromate / 1) dichloromethane, 50 min; 2) benzene, 75 deg C, overnight

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; copper bromide-dimethyl sulfide; 4,4'-di-tert-butylbiphenyl; tetrabutyl ammonium fluoride; lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; butanone; benzene;
DOI:10.1021/ja00211a025

Reference yield:

: 4(R)-(propanoyloxy)-5(S)-(benzyloxy)-6-methylenedihydro-4H-pyran

: 112138-78-0
ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

Guidance literature:: Multi-step reaction with 14 steps

2: 70 percent / p-toluenesulfonic acid / Ambient temperature

3: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

4: 1) oxalyl chloride, dimethyl sulfoxide, (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, RT, overnight

5: 96 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

6: 97 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / Ambient temperature

7: 97 percent / p,p'-di-tert-butylbiphenyl, Li / tetrahydrofuran / -78 °C

8: 93 percent / oxalyl chloride, dimethyl sulfoxide, (i-Pr)2NEt / CH₂Cl₂ / -78 °C

9: 89 percent / n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

10: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

11: 90 percent / (+)-diisopropyltartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH₂Cl₂ / 5 h / -20 °C

12: copper bromide-dimethyl sulfide complex / diethyl ether / 4 h / 0 °C

13: p-toluenesulfonic acid / CHCl₃ / 0.5 h / Ambient temperature

14: 1) pyridinium chlorochromate / 1) dichloromethane, 50 min; 2) benzene, 75 deg C, overnight

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; copper bromide-dimethyl sulfide; 4,4'-di-tert-butylbiphenyl; tetrabutyl ammonium fluoride; lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja00211a025

Reference yield:

: methyl 2-<(1R)-3-methylene-4(S)-(benzyloxy)-1,4-dihydro-3H-pyranyl>propanoate

: 112138-78-0
ethyl 4(R)-<(1R)-4(R)-<(benzyloxy)methyl>-4-hydroxy-3(R),8(S)-dimethyl-2,9-dioxabicyclo<3.3.1>non-5(Z)-en-1-yl>-2-methylpent-2(E)-enoate

Guidance literature:: Multi-step reaction with 13 steps

1: 70 percent / p-toluenesulfonic acid / Ambient temperature

2: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

3: 1) oxalyl chloride, dimethyl sulfoxide, (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, RT, overnight

4: 96 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

5: 97 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / Ambient temperature

6: 97 percent / p,p'-di-tert-butylbiphenyl, Li / tetrahydrofuran / -78 °C

7: 93 percent / oxalyl chloride, dimethyl sulfoxide, (i-Pr)2NEt / CH₂Cl₂ / -78 °C

8: 89 percent / n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

9: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

10: 90 percent / (+)-diisopropyltartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH₂Cl₂ / 5 h / -20 °C

11: copper bromide-dimethyl sulfide complex / diethyl ether / 4 h / 0 °C

12: p-toluenesulfonic acid / CHCl₃ / 0.5 h / Ambient temperature

13: 1) pyridinium chlorochromate / 1) dichloromethane, 50 min; 2) benzene, 75 deg C, overnight

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; copper bromide-dimethyl sulfide; 4,4'-di-tert-butylbiphenyl; tetrabutyl ammonium fluoride; lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja00211a025