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

Base Information

Chemical Name:1,5-anhydro-2-deoxy-3-O-propanoyl-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-gluco-hex-1-enitol
CAS No.:78686-47-2
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

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

Suppliers and Price of 1,5-anhydro-2-deoxy-3-O-propanoyl-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-gluco-hex-1-enitol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of 1,5-anhydro-2-deoxy-3-O-propanoyl-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-gluco-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-2-deoxy-3-O-propanoyl-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-gluco-hex-1-enitol

There total 1 articles about 1,5-anhydro-2-deoxy-3-O-propanoyl-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-gluco-hex-1-enitol 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:

: 79-03-8
propionyl chloride

: 100-39-0
benzyl bromide

: 18162-48-6
tert-butyldimethylsilyl chloride

: 2873-29-2
D-glucal triacetate

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

Guidance literature:: Yield given. Multistep reaction;
DOI:10.1021/ja00401a047

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

: 112138-79-1
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)-en-1-ol

Guidance literature:: Multi-step reaction with 19 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

19: 95 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

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:

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

: 4-<(1R)-3(R)-methoxy-3-methyl-4(R)-<(benzyloxy)methyl>-4-hydroxy-1,4-dihydro-3H-pyran-1-yl>-2(R)-methylpentane-1,3(R)-diol

Guidance literature:: Multi-step reaction with 16 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

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; 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; N,N-dimethyl-formamide; butanone; benzene;
DOI:10.1021/ja00211a025