2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester
CAS No.:195316-50-8
Molecular Formula:C₄₄H₅₆O₉Si
Molecular Weight:757.009
Hs Code.:

2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Synonyms:2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Suppliers and Price of 2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Supply Marketing:

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

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

There total 20 articles about 2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl 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: 80.0%

: 3282-30-2
pivaloyl chloride

: 155369-82-7
(1S,2S)-1-[(2S,3S,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-propane-1,2,3-triol

: 195316-50-8
2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 1h;
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

: 195316-50-8
2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Guidance literature:: Multi-step reaction with 20 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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; DL-10-camphorsulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile;
DOI:10.1248/cpb.45.1265

Reference yield:

: 37776-15-1
6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 195316-50-8
2,2-Dimethyl-propionic acid (2S,3S)-3-[(2S,3S,4R,5R)-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,3-dihydroxy-propyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

2: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

3: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

4: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

5: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

6: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

7: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

8: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

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

10: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

11: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

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

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

14: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

15: 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

16: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

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

18: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

19: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; DL-10-camphorsulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile;
DOI:10.1248/cpb.45.1265