(1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate

Base Information

• Chemical Name: (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate
• CAS No.: 251998-87-5
• Molecular Formula: C₄₀H₇₂O₈S
• Molecular Weight: 713.073
• Mol file: 251998-87-5.mol

Synonyms:(1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate

Chemical Property of (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate

There total 4 articles about (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate 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: 79.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + (1''R,2'R,5'R,2R,6RS)-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexane-1,2,6-triol (251998-85-3) → (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate (251998-87-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(99)01629-9

Reference yield:

(1''R,2'R,5'R,2R,6RS)-1,2-O-isopropylidene-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexane-1,2,6-triol (251998-55-7) → (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate (251998-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / AcOH; H₂O / tetrahydrofuran / 24 h / 20 °C

2: 79 percent / Py / CH₂Cl₂ / 0 - 20 °C

With pyridine; water; acetic acid; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: sulfonylation;

DOI:10.1016/S0040-4020(00)00033-8

Reference yield:

(R)-5-bromo-1,2-O-isopropylidenepentane-1,2-diol (251998-53-5) → (1''R,2'R,5'R,2R,6RS)-2,6-dihydroxy-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexyl 2,4,6-triisopropylbenzenesulfonate (251998-87-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Mg; dibromoethane / diethyl ether / 2 h / 20 °C

1.2: 80 percent / diethyl ether / -78 - 20 °C

2.1: 70 percent / AcOH; H₂O / tetrahydrofuran / 24 h / 20 °C

3.1: 79 percent / Py / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1,1-Dibromoethane; water; magnesium; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Hydrolysis / 3.1: sulfonylation;

DOI:10.1016/S0040-4020(00)00033-8

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

(1''R,2'R,5'R,2R,6RS)-6-(5'-(1''-(methoxymethoxy)tridecyl)tetrahydrofuran-2'-yl)hexane-1,2,6-triol

(R)-5-bromo-1,2-O-isopropylidenepentane-1,2-diol

(4R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol

Refernces

• 1、 Yang, Wen-Qian,Kitahara, Takeshi. "Total synthesis of a nonclassical bioactive acetogenin, (+)-muconin". . p. 1451 - 1461. Retrieved 2007/10/03.