(S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate
• CAS No.: 1001547-77-8
• Molecular Formula: C₂₁H₂₃NO₆S
• Molecular Weight: 417.483
• Mol file: 1001547-77-8.mol

Synonyms:(S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate

Chemical Property of (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate

There total 8 articles about (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate 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%

benzyl (S)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate (1001547-71-2) + p-toluenesulfonyl chloride (98-59-9) → (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate (1001547-77-8)

Guidance literature:

With pyridine; at 24 - 40 ℃; for 22h; Product distribution / selectivity;

Reference yield:

(3R,6R)-hexahydrofuro[3,2-b]furan-3,6-diol → (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate (1001547-77-8)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium hydroxide / tetrachloromethane; dichloromethane; water / 26 h / 0 °C / Inert atmosphere

2: lithium bromide / N,N-dimethyl-formamide / 27 h / 100 °C

3: water; ammonium chloride; zinc / tetrahydrofuran; isopropyl alcohol / 16 h / Inert atmosphere

4: ammonium hydroxide; ammonia; water / isopropyl alcohol / 16 h / 75 °C

5: sodium carbonate / 1,4-dioxane; water / 1.58 h / 0 °C

6: pyridine / 22 h / 24 - 40 °C

With pyridine; ammonium hydroxide; ammonia; water; sodium carbonate; ammonium chloride; potassium hydroxide; lithium bromide; zinc; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

(3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (1001547-69-8) → (S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate (1001547-77-8)

Guidance literature:

Multi-step reaction with 4 steps

1: water; ammonium chloride; zinc / tetrahydrofuran; isopropyl alcohol / 16 h / Inert atmosphere

2: ammonium hydroxide; ammonia; water / isopropyl alcohol / 16 h / 75 °C

3: sodium carbonate / 1,4-dioxane; water / 1.58 h / 0 °C

4: pyridine / 22 h / 24 - 40 °C

With pyridine; ammonium hydroxide; ammonia; water; sodium carbonate; ammonium chloride; zinc; In tetrahydrofuran; 1,4-dioxane; water; isopropyl alcohol;

upstream raw materials:

benzyl (S)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate

p-toluenesulfonyl chloride

(R)-1-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethyl 4-methyl-benzenesulfonate

(3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Downstream raw materials:

C₂₁H₂₃NO₇S

(3R,3aR,6S,6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate

C₁₃H₁₇NO₂

(3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate