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

Base Information

• Chemical Name: ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside
• CAS No.: 400835-47-4
• Molecular Formula: C₂₇H₄₂O₇S
• Molecular Weight: 510.692
• Mol file: 400835-47-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside 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: 95.0%

Isobutyl bromide (78-77-3) + ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-1-thio-α-D-mannopyranoside (189105-30-4) → ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside (400835-47-4)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide;

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) → ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside (400835-47-4)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / dimethylsulfoxide

2: 95 percent / KOH / dimethylsulfoxide

With potassium hydroxide; In 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) → ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside (400835-47-4)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; 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:

Isobutyl bromide

ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-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

Downstream raw materials:

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