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

Base Information

Chemical Name:((2R,3S,3aS,4aS,7S,8aR,9S,9aS)-3,9-Dihydroxy-2-trityloxymethyl-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl)-acetic acid methyl ester
CAS No.:155369-92-9
Molecular Formula:C₃₃H₃₆O₈
Molecular Weight:560.644
Hs Code.:

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

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

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

There total 38 articles about ((2R,3S,3aS,4aS,7S,8aR,9S,9aS)-3,9-Dihydroxy-2-trityloxymethyl-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl)-acetic acid methyl 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:

: 195315-94-7
(4aR,6R,7R,7aR)-6-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-ol

: 155369-92-9
((2R,3S,3aS,4aS,7S,8aR,9S,9aS)-3,9-Dihydroxy-2-trityloxymethyl-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: DMAP, pyridine / CH₂Cl₂ / 1 h

2: 81 percent / imidazole, DMAP / dimethylformamide / 4 h / Ambient temperature

3: 98 percent / DIBAH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

4: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, 1.5 h

5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 45 min

6: 96 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

7: 93 percent / LiAlH₄ / diethyl ether / 0.75 h / 0 °C

8: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

9: 100 percent / dimethylsulfoxide / 1.5 h / 60 °C

10: 100 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

11: 98 percent / CH₂Cl₂ / 9 h / Ambient temperature

12: 67 percent / dl-CSA / methanol / 2.5 h / Ambient temperature

13: TBAF / tetrahydrofuran / 1.5 h / Ambient temperature

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

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; DL-10-camphorsulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.1265

Reference yield:

: 195316-28-0
2-((3aS,4S,5aR,5bS,9aR,10aR,10bR)-2,2,7,7-Tetramethyl-octahydro-1,3,5,6,8,10-hexaoxa-cyclopenta[a]fluoren-4-yl)-ethanol

: 155369-92-9
((2R,3S,3aS,4aS,7S,8aR,9S,9aS)-3,9-Dihydroxy-2-trityloxymethyl-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

2: 100 percent / dimethylsulfoxide / 1.5 h / 60 °C

3: 100 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

4: 98 percent / CH₂Cl₂ / 9 h / Ambient temperature

5: 67 percent / dl-CSA / methanol / 2.5 h / Ambient temperature

6: TBAF / tetrahydrofuran / 1.5 h / Ambient temperature

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

With dmap; DL-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.45.1265

Reference yield:

: 155369-79-2
(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-2-hydroxymethyl-tetrahydro-furan-3-ol

: 155369-92-9
((2R,3S,3aS,4aS,7S,8aR,9S,9aS)-3,9-Dihydroxy-2-trityloxymethyl-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 33 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: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h

13: 80 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.83 h / Ambient temperature

14: 90 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1.5 h / Ambient temperature

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

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

17: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

18: 100 percent / TsOH / benzene; CH₂Cl₂ / 2 h / Ambient temperature

19: 89 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

20: DMAP, pyridine / CH₂Cl₂ / 1 h

21: 81 percent / imidazole, DMAP / dimethylformamide / 4 h / Ambient temperature

22: 98 percent / DIBAH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

23: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, 1.5 h

24: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 45 min

25: 96 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

26: 93 percent / LiAlH₄ / diethyl ether / 0.75 h / 0 °C

27: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

28: 100 percent / dimethylsulfoxide / 1.5 h / 60 °C

29: 100 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

30: 98 percent / CH₂Cl₂ / 9 h / Ambient temperature

31: 67 percent / dl-CSA / methanol / 2.5 h / Ambient temperature

32: TBAF / tetrahydrofuran / 1.5 h / Ambient temperature

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

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; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 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; benzene;
DOI:10.1248/cpb.45.1265