Toluene-4-sulfonic acid 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)-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 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)-ethyl ester
• CAS No.: 195316-29-1
• Molecular Formula: C₂₃H₃₂O₉S
• Molecular Weight: 484.568

Synonyms:Toluene-4-sulfonic acid 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)-ethyl ester

Chemical Property of Toluene-4-sulfonic acid 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)-ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Toluene-4-sulfonic acid 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)-ethyl ester

There total 32 articles about Toluene-4-sulfonic acid 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)-ethyl 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%

p-toluenesulfonyl chloride (98-59-9) + 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 (195316-28-0) → Toluene-4-sulfonic acid 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)-ethyl ester (195316-29-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1248/cpb.45.1265

Reference yield:

(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 (195315-94-7) → Toluene-4-sulfonic acid 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)-ethyl ester (195316-29-1)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

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) → Toluene-4-sulfonic acid 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)-ethyl ester (195316-29-1)

Guidance literature:

Multi-step reaction with 27 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

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; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.45.1265

upstream raw materials:

p-toluenesulfonyl chloride

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

(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

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

Downstream raw materials:

((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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