{2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane
• CAS No.: 195316-35-9
• Molecular Formula: C₅₂H₆₄O₈Si
• Molecular Weight: 845.161

Synonyms:{2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Chemical Property of {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

There total 28 articles about {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S,4R,5R)-3-benzyloxy-5-(2-hydroxyethyl)-2-((1S,2S)-1,2-isopropylidenedioxy-3-trityloxypropyl)-4-(4-methoxybenzyloxy)tetrahydrofuran (195316-07-5) → {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (195316-35-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.45.1265

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (195316-35-9)

Guidance literature:

Multi-step reaction with 27 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: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

21: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

22: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

23: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

24: 96 percent / dimethylsulfoxide / 5 h / 80 °C

25: DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

26: NaBH₄ / tetrahydrofuran; methanol / 4 h / Ambient temperature

27: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; 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; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1248/cpb.45.1265

Reference yield:

benzyl chloride (100-44-7) → {2-[(2R,3R,4S,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane (195316-35-9)

Guidance literature:

Multi-step reaction with 29 steps

1: 1.) NaH / 1.) THF, DMSO, RT, 15 min, 2.) THF, DMSO, RT, 35 min

2: H₂SO₄ / methanol / 0.25 h / Ambient temperature

3: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

5: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

6: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

7: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

8: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

9: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

10: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

11: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

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

13: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

14: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

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

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

17: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

18: 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

19: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

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

21: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

22: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

23: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

24: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

25: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

26: 96 percent / dimethylsulfoxide / 5 h / 80 °C

27: DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

28: NaBH₄ / tetrahydrofuran; methanol / 4 h / Ambient temperature

29: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; 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; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1248/cpb.45.1265

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3S,4R,5R)-3-benzyloxy-5-(2-hydroxyethyl)-2-((1S,2S)-1,2-isopropylidenedioxy-3-trityloxypropyl)-4-(4-methoxybenzyloxy)tetrahydrofuran

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

benzyl chloride

Downstream raw materials:

(2R,3S,4S,5R)-4-Benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-ol

(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-7-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-triethylsilanyloxy-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran

{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Toluene-4-sulfonic acid 2-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-ethyl ester

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