(2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran
• CAS No.: 494212-14-5
• Molecular Formula: C₃₀H₃₄O₄S
• Molecular Weight: 490.664
• Mol file: 494212-14-5.mol

Synonyms:(2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran

Chemical Property of (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran

There total 9 articles about (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran 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: 100.0%

methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-L-erythro-pentopyranoside (494212-13-4) → (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran (494212-14-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1021/jo026163i

Reference yield:

benzyl bromide (100-39-0) → (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran (494212-14-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 16 h / 20 °C

2.1: 96 percent / n-Bu₄NF / tetrahydrofuran / 6 h / 20 °C

3.1: DMSO; oxalyl chloride / CH₂Cl₂ / -78 °C

3.2: Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0 - 23 °C

4.2: 1.91 g / tetrahydrofuran; hexane / -78 - 23 °C

5.1: tetrahydrofuran / 4 h / 0 - 23 °C

6.1: 1.157 g / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

7.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂

With sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Swern oxidation / 4.2: Wittig reaction / 6.1: Suzuki cross-coupling;

DOI:10.1021/jo026163i

Reference yield:

methyl 2-deoxy-α-D-galactopyranoside (3971-45-7) → (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran (494212-14-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 82 percent / imidazole / dimethylformamide / 16 h / 20 °C

2.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 16 h / 20 °C

3.1: 96 percent / n-Bu₄NF / tetrahydrofuran / 6 h / 20 °C

4.1: DMSO; oxalyl chloride / CH₂Cl₂ / -78 °C

4.2: Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0 - 23 °C

5.2: 1.91 g / tetrahydrofuran; hexane / -78 - 23 °C

6.1: tetrahydrofuran / 4 h / 0 - 23 °C

7.1: 1.157 g / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

8.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂

With 1H-imidazole; sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 4.1: Swern oxidation / 5.2: Wittig reaction / 7.1: Suzuki cross-coupling;

DOI:10.1021/jo026163i

upstream raw materials:

methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-L-erythro-pentopyranoside

benzyl bromide

methyl 2-deoxy-α-D-galactopyranoside

methyl 2-deoxy-6-O-(triisopropylsilyl)-α-D-lyxo-hexopyranoside