1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate

Base Information

• Chemical Name: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate
• CAS No.: 220972-34-9
• Molecular Formula: C₁₈H₃₀O₇S
• Molecular Weight: 390.498
• Mol file: 220972-34-9.mol

Synonyms:1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate

Chemical Property of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate

There total 1 articles about 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate 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: 83.0%

Cyclohexanesulfinyl chloride (41719-04-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate (220972-34-9) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (R)-cyclohexanesulfinate

Guidance literature:

With pyridine; In tetrahydrofuran; at -50 ℃; for 2.5h;

DOI:10.1021/jo015956m

Reference yield: 91.0%

N,N-dimethylthioacetamide (631-67-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate (220972-34-9) → (R)-2-(Cyclohexylsulfinyl)-N,N-dimethylethanethioamide (226709-30-4)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) -78 deg C, 30 min;

DOI:10.1055/s-1999-3447

Reference yield: 22.6%

2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate (220972-34-9) → (R,S)-(1,1'-binaphthalene-2,2'-diyl)-bis(cyclohexylsulfoxide) (1268489-67-3) + (M,S,S)-(1,1'-binaphthalene-2,2'-diyl)-bis(cyclohexylsulfoxide) + (P,S,S)-(1,1'-binaphthalene-2,2'-diyl)-bis(cyclohexylsulfoxide)

Guidance literature:

2,2'-dibromo-1,1'-binaphthyl; With n-butyllithium; In tetrahydrofuran; hexane; at -45 ℃; for 0.75h; Inert atmosphere;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201001749

upstream raw materials:

Cyclohexanesulfinyl chloride

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

(R)-2-(Cyclohexylsulfinyl)-N,N-dimethylethanethioamide

(R)-cyclohexyl methyl sulfoxide

(S)-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-1-(prop-2-enylsulfanyl)-(Z)-ethene

(SS,2S,3R)-2-cyclohexylsulfinyl-N,N-dimethyl-3-methylpent-4-enethioamide