(2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan

Base Information

• Chemical Name: (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan
• CAS No.: 182222-77-1
• Molecular Formula: C₂₃H₃₅N₃O₅
• Molecular Weight: 433.548
• Mol file: 182222-77-1.mol

Synonyms:

Chemical Property of (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan

There total 7 articles about (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan 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:

(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol (147910-26-7) → (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan (182222-77-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) TFA, H₂O; 2.) LiAlH₄ / 1.) THF

2: pyridine

3: NaOH / methanol

4: tetrahydrofuran / 0 °C

5: KH / 1,2-dimethoxy-ethane

6: H₂ / Pd(OH)2 / methanol

7: pyridine / CH₂Cl₂ / -20 °C

8: LiN₃ / dimethylformamide

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; lithium azide; water; hydrogen; potassium hydride; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01217-8

Reference yield:

2-{(E)-(S)-1-[(S)-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-methoxymethoxy-methyl]-1-methyl-but-2-enyloxymethyl}-4,4-dimethyl-4,5-dihydro-oxazole → (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan (182222-77-1)

Guidance literature:

Multi-step reaction with 9 steps

1: BuLi / tetrahydrofuran / -78 °C

2: 1.) TFA, H₂O; 2.) LiAlH₄ / 1.) THF

3: pyridine

4: NaOH / methanol

5: tetrahydrofuran / 0 °C

6: KH / 1,2-dimethoxy-ethane

7: H₂ / Pd(OH)2 / methanol

8: pyridine / CH₂Cl₂ / -20 °C

9: LiN₃ / dimethylformamide

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; lithium azide; water; hydrogen; potassium hydride; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01217-8

Reference yield:

(2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-2-((E)-(1R,4S)-1-methoxymethoxy-2-methyl-4-(R)-oxiranyl-pent-2-enyl)-4-methyl-tetrahydro-furan (182222-75-9) → (2S,3R,4S,5S)-3-Azido-5-methoxy-2-((E)-(1R,4S,5S)-5-methoxy-1-methoxymethoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-4-methyl-tetrahydro-furan (182222-77-1)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 0 °C

2: KH / 1,2-dimethoxy-ethane

3: H₂ / Pd(OH)2 / methanol

4: pyridine / CH₂Cl₂ / -20 °C

5: LiN₃ / dimethylformamide

With pyridine; lithium azide; hydrogen; potassium hydride; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01217-8

upstream raw materials:

(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

(2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-2-((E)-(1R,4S)-1-methoxymethoxy-2-methyl-4-(R)-oxiranyl-pent-2-enyl)-4-methyl-tetrahydro-furan

Downstream raw materials:

(2R,3S,4R,5S,6S)-4-Azido-6-methoxy-2-((E)-(3S,4S)-4-methoxy-1,3-dimethyl-5-phenyl-pent-1-enyl)-5-methyl-tetrahydro-pyran-3-ol