(2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol
• CAS No.: 400835-48-5
• Molecular Formula: C₁₉H₃₀O₅S
• Molecular Weight: 370.51
• Mol file: 400835-48-5.mol

Synonyms:(2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol

Chemical Property of (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol

There total 7 articles about (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol 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: 80.0%

ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside (400835-47-4) → (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol (400835-48-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jm020487h

Reference yield:

(1'S,2'S)-Ethyl 3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1-thio-α-D-mannopyranoside (163125-38-0) → (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol (400835-48-5)

Guidance literature:

Multi-step reaction with 3 steps

1: KOH / dimethylsulfoxide

2: 95 percent / KOH / dimethylsulfoxide

3: 80 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With potassium hydroxide; trifluoroacetic acid; In dichloromethane; dimethyl sulfoxide; 1: Williamson reaction / 2: Williamson reaction;

DOI:10.1021/jm020487h

Reference yield:

ethyl 1-thio-α-D-mannopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol (400835-48-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 43 percent / CSA; TMOF / methanol

2: 85 percent / imidazole / dimethylformamide

3: 96 percent / KN(SiMe₃)2

4: 96 percent / TBAF / tetrahydrofuran

5: 89 percent / KN(SiMe₃)2

6: 73 percent / 90 percent TFA

With 1H-imidazole; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; trifluoroacetic acid; trimethyl orthoformate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20011015)40:20<3870::AID-ANIE3870>3.0.CO;2-X

upstream raw materials:

ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside

benzyl bromide

(1'S,2'S)-Ethyl 3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1-thio-α-D-mannopyranoside

ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-1-thio-α-D-mannopyranoside

Downstream raw materials:

ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside