(2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 1054752-77-0
• Molecular Formula: C₄₁H₅₉ClO₇Si
• Molecular Weight: 727.454

Synonyms:(2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property of (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

There total 26 articles about (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde 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:

(4'S)-2-(2',2'-dimethyl[1',3']dioxolan-4'-ylmethyl)propenal (1059575-06-2) → (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde (1054752-77-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 83 percent / NaBH₄, CeCl₃*H₂O / CH₂Cl₂; methanol / -78 °C

3: TBAF / tetrahydrofuran

4: 91 percent / Et₃N, DMAP / CH₂Cl₂

5: 81 percent / KH / dimethylformamide; tetrahydrofuran / 0 - 20 °C

6: 56 percent / aq. ZnBr₂ / CH₂Cl₂

7: 80 percent / pyridine, DMAP

8: 91 percent / 2,6-lutidine / CH₂Cl₂

9: 61 percent / LAH / tetrahydrofuran / -78 °C

10: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 0 deg C

11: 1.) In, NaI / 1.) DMF, 2.) DMF

12: Martin's sulfurane / CH₂Cl₂

13: 76 percent / hydrogen fluoride pyridine complex, pyridine / tetrahydrofuran

14: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 0 deg C

With pyridine; 2,6-dimethylpyridine; dmap; indium; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; oxalyl dichloride; Martins sulfurane; tetrabutyl ammonium fluoride; potassium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; sodium iodide; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<190::aid-anie190>3.0.co;2-0

Reference yield:

3-Methyl-1-triisopropylsilanyloxy-pent-4-en-2-ol → (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde (1054752-77-0)

Guidance literature:

Multi-step reaction with 23 steps

1: 84 percent / NaH, TBAI / tetrahydrofuran / 0 - 20 °C

2: N-methylmorpholine N-oxide, OsO₄, H₂O / tetrahydrofuran

3: aq. NaIO₄ / methanol / 0 - 20 °C

4: toluene / -78 °C

5: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6: Li, NH₃ / tetrahydrofuran / -78 °C

7: N-methylmorpholine N-oxide, OsO₄, H₂O / tetrahydrofuran

8: aq. NaIO₄ / methanol / 0 - 20 °C

9: 1.) diketene acetone adduct, Et₃N / 1.) hexane, 70 deg C, 2.) 125 deg C, 0.2 Torr

10: dimethyldioxirane / CH₂Cl₂; acetone / -10 °C

12: TBAF / tetrahydrofuran

13: 91 percent / Et₃N, DMAP / CH₂Cl₂

14: 81 percent / KH / dimethylformamide; tetrahydrofuran / 0 - 20 °C

15: 56 percent / aq. ZnBr₂ / CH₂Cl₂

16: 80 percent / pyridine, DMAP

17: 91 percent / 2,6-lutidine / CH₂Cl₂

18: 61 percent / LAH / tetrahydrofuran / -78 °C

19: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 0 deg C

20: 1.) In, NaI / 1.) DMF, 2.) DMF

21: Martin's sulfurane / CH₂Cl₂

22: 76 percent / hydrogen fluoride pyridine complex, pyridine / tetrahydrofuran

23: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 0 deg C

With pyridine; 2,6-dimethylpyridine; dmap; indium; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; Martins sulfurane; diketene acetone; tetrabutyl ammonium fluoride; ammonia; water; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; lithium; potassium hydride; sodium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<190::aid-anie190>3.0.co;2-0

Reference yield:

(S)-2-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)prop-2-en-1-ol → (2R,3R,4R,5R,6R)-6-((E)-(S)-7-Chloro-2-methylene-4-triisopropylsilanyloxy-octa-5,7-dienyl)-4,5-bis-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde (1054752-77-0)

Guidance literature:

Multi-step reaction with 13 steps

2: TBAF / tetrahydrofuran

3: 91 percent / Et₃N, DMAP / CH₂Cl₂

4: 81 percent / KH / dimethylformamide; tetrahydrofuran / 0 - 20 °C

5: 56 percent / aq. ZnBr₂ / CH₂Cl₂

6: 80 percent / pyridine, DMAP

7: 91 percent / 2,6-lutidine / CH₂Cl₂

8: 61 percent / LAH / tetrahydrofuran / -78 °C

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 0 deg C

10: 1.) In, NaI / 1.) DMF, 2.) DMF

11: Martin's sulfurane / CH₂Cl₂

12: 76 percent / hydrogen fluoride pyridine complex, pyridine / tetrahydrofuran

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 0 deg C

With pyridine; 2,6-dimethylpyridine; dmap; indium; lithium aluminium tetrahydride; oxalyl dichloride; Martins sulfurane; tetrabutyl ammonium fluoride; potassium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; sodium iodide; zinc dibromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<190::aid-anie190>3.0.co;2-0

upstream raw materials:

(4'S)-2-(2',2'-dimethyl[1',3']dioxolan-4'-ylmethyl)propenal

Downstream raw materials:

C₆₉H₁₁₇ClO₁₀Si₃

C₆₁H₁₀₃ClO₁₁Si₃

C₆₂H₉₅ClO₁₃SSi₂

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