(1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid

Base Information

• Chemical Name: (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid
• CAS No.: 440641-45-2
• Molecular Formula: C₂₅H₃₂O₉
• Molecular Weight: 476.524
• Mol file: 440641-45-2.mol

Synonyms:(1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid

Chemical Property of (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid

There total 31 articles about (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid 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: 88.0%

(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane (215173-36-7) → (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid (440641-45-2)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In water; acetonitrile; at 20 ℃; for 5h;

DOI:10.1021/jo011157s

Reference yield: 67.0%

trimethyl (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-((trimethylsilyl)oxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate → (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid (440641-45-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01513

Reference yield:

Dimethyl D-tartrate (13171-64-7) → (1S,3S,4S,5R)-1-((R,E)-3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxylic acid (440641-45-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 62 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 72 h

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

2.2: NaBH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

4.1: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

6.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

7.1: 89 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

8.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -78 - 0 °C

8.2: Al(Hg) / hexamethylphosphoric acid triamide; tetrahydrofuran; H₂O / 3 h / 20 °C

8.3: 7.6 mg / aq. H₂SO₄ / methanol / 40 h / 20 °C

9.1: 88 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / acetonitrile; H₂O / 5 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; tetrapropylammonium perruthennate; dimethylsulfide borane complex; hydrogen; dimethylaluminum chloride; pyridinium p-toluenesulfonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetonitrile; 6.1: Dess-Martin oxidation;

DOI:10.1021/jo011157s

upstream raw materials:

(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

Dimethyl D-tartrate

(2S,3R)-3,4-Dihydroxy-2-(tetrahydro-pyran-2-yloxy)-butyric acid methyl ester

dimethyl O-tetrahydro-2H-pyran-2-yl-D-tartrate