2(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>propan-1-ol

Base Information

Chemical Name:2(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>propan-1-ol
CAS No.:112138-76-8
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:2(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>propan-1-ol

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Chemical Property of 2(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>propan-1-ol

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Technology Process of 2(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>propan-1-ol

There total 17 articles about 2(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>propan-1-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:

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

: 112138-76-8
2(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>propan-1-ol

Guidance literature:: Multi-step reaction with 17 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

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; 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

: 112138-76-8
2(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>propan-1-ol

Guidance literature:: Multi-step reaction with 13 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

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; 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

: 112138-76-8
2(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>propan-1-ol

Guidance literature:: Multi-step reaction with 12 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

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; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja00211a025