(E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester
• CAS No.: 181266-50-2
• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.537
• Mol file: 181266-50-2.mol

Synonyms:(E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester

Chemical Property of (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester

There total 14 articles about (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid 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:

ethyl (diisopropylphosphoryl)acetate (24074-26-8) + (R)-2-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-propionaldehyde → (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester (181266-50-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; Yield given;

Reference yield:

1,5-Anhydro-4,6-O-benzyliden-2-desoxy-D-arabinohexitol (33640-16-3) → (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester (181266-50-2)

Guidance literature:

Multi-step reaction with 12 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

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; phosgene; dmap; sodium periodate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

4,6-O-benzylidene-1,2-dideoxy-D-glucose (13035-13-7) → (E)-(S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl ester (181266-50-2)

Guidance literature:

Multi-step reaction with 14 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

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; phosgene; dmap; sodium periodate; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; potassium tert-butylate; L-Selectride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

ethyl (diisopropylphosphoryl)acetate

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

Downstream raw materials:

(E)-(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-dodec-7-en-6-one

(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

(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

(2R,3R,4S)-4-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,3-diol