2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
CAS No.:195316-25-7
Molecular Formula:C₂₃H₃₄O₈
Molecular Weight:438.518
Hs Code.:

2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Synonyms:2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Suppliers and Price of 2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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 2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 26 articles about 2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 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: 100.0%

: 195315-93-6
2,2-Dimethyl-propionic acid (4S,5S)-5-[(2R,3S,4S,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 195316-25-7
2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1248/cpb.45.1265

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 195316-25-7
2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 25 steps

1: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

3: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

4: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

5: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

6: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

7: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

8: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

9: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

10: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

11: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

12: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

13: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

14: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

15: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

16: 1.) D-(-)-diethyl tartrate, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) CH₂Cl₂, 2,2,4-trimethylpentane, 3 d

17: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

18: BF₃*Et₂O / diethyl ether / 2 h / 0 °C

19: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

20: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h

21: 80 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.83 h / Ambient temperature

22: 90 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1.5 h / Ambient temperature

23: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 45 min

24: NaBH₄ / tetrahydrofuran; methanol / 0.67 h / -78 °C

25: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; DL-10-camphorsulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile;
DOI:10.1248/cpb.45.1265

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 195316-25-7
2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 26 steps

1: H₂SO₄ / methanol / 0.25 h / Ambient temperature

2: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

4: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

5: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

6: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

7: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

8: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

9: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

10: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

11: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

12: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

13: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

14: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

15: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

16: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

17: 1.) D-(-)-diethyl tartrate, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) CH₂Cl₂, 2,2,4-trimethylpentane, 3 d

18: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

19: BF₃*Et₂O / diethyl ether / 2 h / 0 °C

20: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

21: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h

22: 80 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.83 h / Ambient temperature

23: 90 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1.5 h / Ambient temperature

24: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 45 min

25: NaBH₄ / tetrahydrofuran; methanol / 0.67 h / -78 °C

26: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; DL-10-camphorsulfonic acid; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile;
DOI:10.1248/cpb.45.1265