(2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol

Base Information

• Chemical Name: (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol
• CAS No.: 195316-47-3
• Molecular Formula: C₃₃H₃₈O₇
• Molecular Weight: 546.661

Synonyms:(2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol

Chemical Property of (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol

There total 45 articles about (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol 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%

[(2R,3S,3aS,4aS,7R,8aR,9S,9aS)-3,9-Dihydroxy-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester (195316-15-5) → (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol (195316-47-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1248/cpb.45.1265

Reference yield:

(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-2-hydroxymethyl-tetrahydro-furan-3-ol (155369-79-2) → (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol (195316-47-3)

Guidance literature:

Multi-step reaction with 41 steps

1: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

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

3: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

4: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

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

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

7: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8: 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

9: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

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

11: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

12: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

13: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

14: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

15: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

16: 96 percent / dimethylsulfoxide / 5 h / 80 °C

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

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

19: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

20: 95 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1 h / Ambient temperature

21: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 1 h

22: NaBH₄ / tetrahydrofuran; methanol / 1.5 h / -78 °C

23: 97 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 33 h / 40 °C

24: 94 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

25: 97 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

26: 98 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

27: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

28: 100 percent / imidazole, DMAP / dimethylformamide / 15 h / 40 °C

29: 99 percent / DIBAH / CH₂Cl₂; hexane / 1.5 h / -78 °C

30: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 20 min

31: 1.) tert-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 40 min

32: 98 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

33: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

34: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h

35: 100 percent / dimethylsulfoxide / 3.3 h / 60 °C

36: 95 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

37: 100 percent / CH₂Cl₂ / 15 h / Ambient temperature

38: dl-CSA / methanol / 60 h / Ambient temperature

39: TBAF / tetrahydrofuran / 24 h

40: 1.) Et₃N, DMAP, 2.) TBAF / 1.) CH₂Cl₂, RT, 14 h, 2.) THF, RT, 15 h

41: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; 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; ammonia; sodium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.45.1265

Reference yield:

(E)-5-[(2R,3S,3aS,5S,6R,7S,7aS)-3,6,7-Trihydroxy-2-(2-hydroxy-ethyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid methyl ester (1053631-82-5) → (2R,3S,3aS,4aS,7R,8aR,9S,9aS)-7-(2-Hydroxy-ethyl)-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-3,9-diol (195316-47-3)

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran / 24 h

2: 1.) Et₃N, DMAP, 2.) TBAF / 1.) CH₂Cl₂, RT, 14 h, 2.) THF, RT, 15 h

3: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

With dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1248/cpb.45.1265

upstream raw materials:

[(2R,3S,3aS,4aS,7R,8aR,9S,9aS)-3,9-Dihydroxy-2-(2-trityloxy-ethyl)-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-2-hydroxymethyl-tetrahydro-furan-3-ol

(E)-5-[(2R,3S,3aS,5S,6R,7S,7aS)-3,6,7-Trihydroxy-2-(2-hydroxy-ethyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid methyl ester

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

Downstream raw materials:

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

(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

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