5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

Base Information

Chemical Name:5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid
CAS No.:147806-88-0
Molecular Formula:C₃₄H₅₀O₇Si
Molecular Weight:598.852
Hs Code.:

Synonyms:5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

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Chemical Property of 5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

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Technology Process of 5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

There total 24 articles about 5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid 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: 92.0%

: 143293-32-7
methyl 5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconate

: 147806-88-0
5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 50 ℃; for 1h;

Reference yield:

: 132375-56-5
((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

: 147806-88-0
5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

Guidance literature:: Multi-step reaction with 18 steps

1: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

2: 98 percent / TFA / toluene / 0.25 h / 0 °C

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

4: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

6: benzene / 2 h / 80 °C

7: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

8: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

9: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

10: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

11: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

12: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

13: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

14: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

15: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

16: 89 percent / benzene / 3 h / 25 °C

17: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

18: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; sodium hydroxide; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; benzene;

Reference yield:

: 122821-81-2
2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

: 147806-88-0
5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-6-O-(tert-butyldimethylsilyl)-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid

Guidance literature:: Multi-step reaction with 19 steps

1: 80 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

2: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

3: 98 percent / TFA / toluene / 0.25 h / 0 °C

4: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

5: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

7: benzene / 2 h / 80 °C

8: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

9: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

10: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

11: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

12: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

13: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

14: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

15: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

16: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

17: 89 percent / benzene / 3 h / 25 °C

18: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

19: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; sodium hydroxide; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; benzene;