(2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol

Base Information

• Chemical Name: (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol
• CAS No.: 181267-20-9
• Molecular Formula: C₅₄H₆₈O₇
• Molecular Weight: 829.13

Synonyms:(2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol

Chemical Property of (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol

There total 37 articles about (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol 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: 94.0%

(2R,4S,5S,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-one (181267-15-2) → (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol (181267-20-9)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at -15 ℃;

Reference yield:

1,5-Anhydro-4,6-O-benzyliden-2-desoxy-D-arabinohexitol (33640-16-3) → (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol (181267-20-9)

Guidance literature:

Multi-step reaction with 24 steps

1: NaH / dimethylformamide / Ambient temperature

2: 94 percent / p-TsOH, MeOH / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

4: NaH / dimethylformamide / Ambient temperature

5: p-TsOH, MeOH / Ambient temperature

6: 1.) (COCl₂), DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) r.t.

7: benzene / Ambient temperature

8: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9: 85 percent / t-BuOOH, Ti(O-i-Pr)4, (+)-diethyl L-tartrate, molecular sieves 4 Angstroem / -20 °C

10: CH₂Cl₂; hexane / 0 °C

11: aq. NaIO₄ / tetrahydrofuran / Ambient temperature

12: t-BuOK / tetrahydrofuran / -78 °C

13: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

14: 85 percent / t-BuOOH, Ti(O-i-Pr)4, (-)-diethyl D-tartrate, molecular sieves 4 Angstroem / -20 °C

15: diethyl ether / -20 °C

16: 82 percent / (i-Pr)2NEt, DMAP / CH₂Cl₂ / Ambient temperature

17: NaH, TBAI / dimethylformamide / Ambient temperature

18: p-TsOH, MeOH / Ambient temperature

19: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) r.t.

20: CrCl₂ / tetrahydrofuran / 0 °C

21: 52 percent / CrCl₂, NiCl₂ / dimethylsulfoxide / Ambient temperature

22: 91 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

23: 79 percent / NaHTe / ethanol / Ambient temperature

24: 94 percent / Zn(BH₄)2 / diethyl ether / -15 °C

With chromium dichloride; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; phosgene; dmap; sodium periodate; dipyridinium dichromate; zinc(II) tetrahydroborate; oxalyl dichloride; sodium hydrogen telluride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

4,6-O-benzylidene-1,2-dideoxy-D-glucose (13035-13-7) → (2R,4S,5S,6R,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-ol (181267-20-9)

Guidance literature:

Multi-step reaction with 26 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) r.t.

2: L-Selectride / tetrahydrofuran / -78 °C

3: NaH / dimethylformamide / Ambient temperature

4: 94 percent / p-TsOH, MeOH / Ambient temperature

5: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

6: NaH / dimethylformamide / Ambient temperature

7: p-TsOH, MeOH / Ambient temperature

8: 1.) (COCl₂), DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) r.t.

9: benzene / Ambient temperature

10: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

11: 85 percent / t-BuOOH, Ti(O-i-Pr)4, (+)-diethyl L-tartrate, molecular sieves 4 Angstroem / -20 °C

12: CH₂Cl₂; hexane / 0 °C

13: aq. NaIO₄ / tetrahydrofuran / Ambient temperature

14: t-BuOK / tetrahydrofuran / -78 °C

15: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

16: 85 percent / t-BuOOH, Ti(O-i-Pr)4, (-)-diethyl D-tartrate, molecular sieves 4 Angstroem / -20 °C

17: diethyl ether / -20 °C

18: 82 percent / (i-Pr)2NEt, DMAP / CH₂Cl₂ / Ambient temperature

19: NaH, TBAI / dimethylformamide / Ambient temperature

20: p-TsOH, MeOH / Ambient temperature

21: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) r.t.

22: CrCl₂ / tetrahydrofuran / 0 °C

23: 52 percent / CrCl₂, NiCl₂ / dimethylsulfoxide / Ambient temperature

24: 91 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

25: 79 percent / NaHTe / ethanol / Ambient temperature

26: 94 percent / Zn(BH₄)2 / diethyl ether / -15 °C

With chromium dichloride; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; phosgene; dmap; sodium periodate; dipyridinium dichromate; zinc(II) tetrahydroborate; oxalyl dichloride; sodium hydrogen telluride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(2R,4S,5S,9S,10S,11S)-2,5,10-Tris-benzyloxy-11-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-4,9-dimethyl-dodecan-6-one

1,5-Anhydro-4,6-O-benzyliden-2-desoxy-D-arabinohexitol

4,6-O-benzylidene-1,2-dideoxy-D-glucose

O-benzyl 2,2,2-trichloroacetimidate

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