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

Base Information

Chemical Name:methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside
CAS No.:494212-06-5
Molecular Formula:C₃₀H₃₄O₄S
Molecular Weight:490.664
Hs Code.:

Synonyms:methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside

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Chemical Property of methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside

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Technology Process of methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside

There total 8 articles about methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside 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:

: 61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0
2-deoxy-D-arabino-hexopyranose

: 494212-06-5
methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / AcCl / 4 h / 23 °C

2.1: 70 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 16 h / 20 °C

4.1: 95 percent / n-Bu₄NF / tetrahydrofuran / 6 h / 20 °C

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

5.2: Et₃N / CH₂Cl₂ / -78 - 0 °C

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

6.2: 1.37 g / tetrahydrofuran; hexane / -78 - 23 °C

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

8.1: 1.07 g / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

With 1H-imidazole; sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; acetyl chloride; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 5.1: Swern oxidation / 6.2: Wittig reaction / 8.1: Suzuki cross-coupling;
DOI:10.1021/jo026163i

Reference yield:

: 160400-66-8
methyl 2-deoxy-D-arabinopyranoside

: 494212-06-5
methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / imidazole / dimethylformamide / 16 h / 20 °C

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

3.1: 95 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: 1.37 g / tetrahydrofuran; hexane / -78 - 23 °C

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

7.1: 1.07 g / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

With 1H-imidazole; sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; 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

Reference yield:

: 145149-85-5
Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside

: 494212-06-5
methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: Et₃N / CH₂Cl₂ / -78 - 0 °C

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

2.2: 1.37 g / tetrahydrofuran; hexane / -78 - 23 °C

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

4.1: 1.07 g / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

With sodium hydroxide; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; benzene; 1.1: Swern oxidation / 2.2: Wittig reaction / 4.1: Suzuki cross-coupling;
DOI:10.1021/jo026163i