(2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran
• CAS No.: 181489-34-9
• Molecular Formula: C₃₃H₃₉IO₄
• Molecular Weight: 626.575
• Mol file: 181489-34-9.mol

Synonyms:

Chemical Property of (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran

There total 22 articles about (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran 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:

(2S,3S,4S)-3-Benzyloxy-4-((2R,3S,4S)-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-methyl-pentanal + methyl iodide (74-88-4) → (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran (181489-34-9)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; at 0 ℃;

Reference yield:

1,5-Anhydro-4,6-O-benzyliden-2-desoxy-D-arabinohexitol (33640-16-3) → (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran (181489-34-9)

Guidance literature:

Multi-step reaction with 20 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: t-BuOOH, Ti(O-i-Pr)4, (+)-diethyl L-tartrate, molecular sieves 4 Angstroem / -20 °C

15: diethyl ether / -20 °C

16: (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

With chromium dichloride; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; phosgene; dmap; sodium periodate; oxalyl dichloride; 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; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

4,6-O-benzylidene-1,2-dideoxy-D-glucose (13035-13-7) → (2R,3S,4S)-3,4-Bis-benzyloxy-2-((E)-(1S,2R,3R)-2-benzyloxy-5-iodo-1,3-dimethyl-pent-4-enyl)-tetrahydro-pyran (181489-34-9)

Guidance literature:

Multi-step reaction with 22 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: t-BuOOH, Ti(O-i-Pr)4, (+)-diethyl L-tartrate, molecular sieves 4 Angstroem / -20 °C

17: diethyl ether / -20 °C

18: (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

With chromium dichloride; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; phosgene; dmap; sodium periodate; oxalyl dichloride; 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; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

methyl iodide

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

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

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-erythro-hex-3-ulose