(3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate

Base Information

• Chemical Name: (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate
• CAS No.: 1365659-13-7
• Molecular Formula: C₂₂H₂₇NO₇S
• Molecular Weight: 449.525
• Mol file: 1365659-13-7.mol

Synonyms:(3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate

Chemical Property of (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate

There total 10 articles about (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate 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: 90.3%

benzyl benzyl(((3R)-hydroxy-2(R/S)-methoxy-(5S)-tetrahydrofuran2-yl)methyl)carbamate (1365659-12-6) + methanesulfonyl chloride (124-63-0) → (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate (1365659-13-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1080/00397911.2010.539753

Reference yield:

C15H19NO3 (1255906-08-1) → (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate (1365659-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium tetrahydroborate / methanol / 1 h / 20 °C

2: sodium carbonate / dichloromethane; water / 4 h / 20 °C

3: toluene-4-sulfonic acid / methanol / 0 - 20 °C

4: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium carbonate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; water;

DOI:10.1080/00397911.2010.539753

Reference yield:

O1,O2-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose (4613-68-7,14260-67-4,22248-90-4,74996-06-8) → (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate (1365659-13-7)

Guidance literature:

Multi-step reaction with 5 steps

1: magnesium sulfate / dichloromethane / 5 h / 20 °C

2: sodium tetrahydroborate / methanol / 1 h / 20 °C

3: sodium carbonate / dichloromethane; water / 4 h / 20 °C

4: toluene-4-sulfonic acid / methanol / 0 - 20 °C

5: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium carbonate; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; water;

DOI:10.1080/00397911.2010.539753

upstream raw materials:

O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose

C₁₅H₁₉NO₃

N-benzyl-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanamine

benzyl benzyl((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)carbamate