(5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate

Base Information

• Chemical Name: (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate
• CAS No.: 866343-41-1
• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.493
• Mol file: 866343-41-1.mol

Synonyms:(5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate

Chemical Property of (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate

There total 15 articles about (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate 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: 97.0%

tert-butyl (5S,6S,E)-5-(allyloxy)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-hept-2-enoate (866343-51-3) → (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate (866343-41-1)

Guidance literature:

With p-toluene sulfinic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/chem.200500282

Reference yield: 96.0%

(2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol (932739-33-8) + tert-Butyl acrylate (1663-39-4,25232-27-3) → (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate (866343-41-1)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 15h; diastereoselective reaction; Reflux; Darkness;

DOI:10.1021/ol1000473

Reference yield:

methyl (R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanoate (932739-31-6) → (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate (866343-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 °C

2.1: MgBr₂*Et₂O / CH₂Cl₂ / 0.25 h / -78 °C

2.2: 77 percent / CH₂Cl₂ / 12 h / -78 °C

3.1: 71 percent / second generation Grubbs catalyst / CH₂Cl₂ / 19 h / 20 °C

With diisobutylaluminium hydride; magnesium bromide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; toluene;

DOI:10.1021/ol063032l

upstream raw materials:

tert-butyl (5S,6S,E)-5-(allyloxy)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-hept-2-enoate

(2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol

tert-Butyl acrylate

(R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanal

Downstream raw materials:

(E)-(5S,6S)-5-((S)-2-{3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2,2-dimethyl-propionyloxy}-4-methyl-pentanoyloxy)-6-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-hept-2-enoic acid tert-butyl ester

(E)-(5S,6S)-5-((S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-hept-2-enoic acid tert-butyl ester

cryptophycin-1

(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone