{(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane

Base Information

• Chemical Name: {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane
• CAS No.: 123363-73-5
• Molecular Formula: C₃₅H₅₆O₄Si
• Molecular Weight: 568.913
• Mol file: 123363-73-5.mol

Synonyms:{(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane

Chemical Property of {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane

There total 11 articles about {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane 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: 67.0%

[(Z)-(1R,2R)-1-((1S,2R,3R)-2,4-Bis-benzyloxy-1,3-dimethyl-butyl)-2-methyl-pent-3-enyloxy]-triisopropyl-silane (123363-72-4) → {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane (123363-73-5)

Guidance literature:

With WO₅*HMPA; In dichloromethane; Ambient temperature;

DOI:10.1246/cl.1989.117

Reference yield:

(Z)-(3R,4R)-3-Hydroxy-4-methyl-hept-5-enal → {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane (123363-73-5)

Guidance literature:

Multi-step reaction with 10 steps

1: NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / from -5 deg C to RT

2: diethyl ether / Ambient temperature

3: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -50 - -20 °C

4: LAH / tetrahydrofuran / 0 °C

5: 60 percent / VO(acac)2, TBHP / CH₂Cl₂ / from -20 deg C to RT

6: NaH / tetrahydrofuran; dimethylformamide / 50 °C

7: BF₃*OEt₂ / tetrahydrofuran / from -78 deg C to -20 deg C

8: H₂, quinoline / Pd-CaCO₃ / benzene / Ambient temperature

9: 2,6-dimethylpyridine / CH₂Cl₂ / Ambient temperature

10: 67 percent / WO₅*HMPA / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; quinoline; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; bis(acetylacetonate)oxovanadium; WO₅*HMPA; boron trifluoride diethyl etherate; hydrogen; sodium hydride; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1989.117

Reference yield:

(2R,3R,4S)-2-Methyl-4-((2S,3R)-3-methyl-oxiranyl)-pentane-1,3-diol (123363-70-2,123410-28-6) → {(1R,2R,3S,4S)-3,5-Bis-benzyloxy-2,4-dimethyl-1-[(S)-1-((2S,3R)-3-methyl-oxiranyl)-ethyl]-pentyloxy}-triisopropyl-silane (123363-73-5)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran; dimethylformamide / 50 °C

2: BF₃*OEt₂ / tetrahydrofuran / from -78 deg C to -20 deg C

3: H₂, quinoline / Pd-CaCO₃ / benzene / Ambient temperature

4: 2,6-dimethylpyridine / CH₂Cl₂ / Ambient temperature

5: 67 percent / WO₅*HMPA / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; quinoline; WO₅*HMPA; boron trifluoride diethyl etherate; hydrogen; sodium hydride; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1246/cl.1989.117

upstream raw materials:

[(Z)-(1R,2R)-1-((1S,2R,3R)-2,4-Bis-benzyloxy-1,3-dimethyl-butyl)-2-methyl-pent-3-enyloxy]-triisopropyl-silane

(2R,3R,4S)-2-Methyl-4-((2S,3R)-3-methyl-oxiranyl)-pentane-1,3-diol

(Z)-(2R,3S,4R)-2,4-Dimethyl-hept-5-ene-1,3-diol

(Z)-(3R,4R)-3-Hydroxy-4-methyl-hept-5-enoic acid methyl ester

Downstream raw materials:

(2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

(2R,3R,4R,5R,6S,7R,8R)-5,7,9-Tris-benzyloxy-2-[1,3]dithian-2-yl-4,6,8-trimethyl-nonan-3-ol