(4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone

Base Information

• Chemical Name: (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone
• CAS No.: 110995-47-6
• Molecular Formula: C₂₂H₂₂O₅S
• Molecular Weight: 398.48
• Mol file: 110995-47-6.mol

Synonyms:(4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone

Chemical Property of (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone

There total 6 articles about (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone 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: 87.0%

(4R,5R)-(2Z)-N-methyl-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-erythro-hex-2-enonamide (110995-45-4) → (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone (110995-47-6)

Guidance literature:

In octane; Heating;

DOI:10.1016/S0040-4039(00)85273-9

Reference yield:

(Z)-2-(benzyloxy)-N-methyl-3-(phenylthio)acrylamide (90461-25-9) → (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone (110995-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) diisopropylamine, n-butyllithium / 1.) THF, HMPA, -78 deg C, 2 h; 2.) THF, -78 deg C -> 0 deg C, 1 h

2: 87 percent / octane / 4 h / Heating

With n-butyllithium; diisopropylamine; In octane;

DOI:10.1016/S0040-4020(01)89133-X

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (4R,5R)-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-γ-hex-2-enolactone (110995-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) diisopropylamine, n-butyllithium / 1.) THF, HMPA, -78 deg C, 2 h; 2.) THF, -78 deg C -> 0 deg C, 1 h

2: 87 percent / octane / 4 h / Heating

With n-butyllithium; diisopropylamine; In octane;

DOI:10.1016/S0040-4020(01)89133-X

upstream raw materials:

(4R,5R)-(2Z)-N-methyl-5,6-O-(1-methylethylidene)-3-S-phenyl-2-O-(phenylmethyl)-3-thio-erythro-hex-2-enonamide

(Z)-2-(benzyloxy)-N-methyl-3-(phenylthio)acrylamide

2,3-isopropylidene-glyceraldehyde

ethyl 2-(benzyloxy)acrylate

Downstream raw materials:

(4R,5R)-5,6-O-(1-methylethylidene)-2-O-(phenylmethyl)-γ-hex-2-enolactone