cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside

Base Information

• Chemical Name: cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside
• CAS No.: 131922-38-8
• Molecular Formula: C₁₇H₂₆O₆S
• Molecular Weight: 358.456
• Mol file: 131922-38-8.mol

Synonyms:cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside

Chemical Property of cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside

There total 4 articles about cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside 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:

3,4-di-O-acetyl-2,6-anhydro-1-fluoro-2-thio-D-altropyranoside (131922-22-0,131922-37-7) + cyclohexylmethyl alcohol (100-49-2) → cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-α-D-altropyranoside (130427-29-1) + cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside (131922-38-8)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; tin(ll) chloride; In diethyl ether; at -10 ℃; for 1.5h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00099a022

Reference yield:

1,3,4-tri-O-acetyl-2,6-anhydro-2-thio-D-β-altropyranoside (141299-49-2) + cyclohexylmethyl alcohol (100-49-2) → cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-α-D-altropyranoside (130427-29-1) + cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside (131922-38-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -10 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)91656-3

Reference yield:

methyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-D-α-altropyranoside (18439-47-9) → cyclohexylmethyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside (131922-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / conc. H₂SO₄ / 0.17 h / 0 °C

2: TMSOTf / CH₂Cl₂ / 0.5 h / -10 °C / different solvents, various Lewis acids, other reaction time

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)91656-3

upstream raw materials:

3,4-di-O-acetyl-2,6-anhydro-1-fluoro-2-thio-D-altropyranoside

cyclohexylmethyl alcohol

1,3,4-tri-O-acetyl-2,6-anhydro-2-thio-D-β-altropyranoside

methyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-D-α-altropyranoside

Downstream raw materials:

(2R,3S,4S,6R)-6-Cyclohexylmethoxy-2-methyl-tetrahydro-pyran-3,4-diol

Acetic acid (2R,3R,4S,6R)-3-acetoxy-6-cyclohexylmethoxy-2-methyl-tetrahydro-pyran-4-yl ester