Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 1053622-69-7
• Molecular Formula: C₂₁H₃₃NO₈S
• Molecular Weight: 459.561
• Mol file: 1053622-69-7.mol

Synonyms:

Chemical Property of Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 13 articles about Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 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:

(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol (869660-99-1) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (1053622-69-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.08.039

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-4-oxiranyl-D-arabinitol (869660-95-7) → Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (1053622-69-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: magnesium; iodine / tetrahydrofuran

1.2: 86 percent / copper(I) iodide / tetrahydrofuran / 0 - 20 °C

2.1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

3.1: 550 mg / sodium azide; 18-crown-6 / dimethylsulfoxide / 24 h / 65 °C

4.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

5.1: 450 mg / triethylamine / tetrahydrofuran / 6 h / 20 °C

6.1: 83 percent / lithium; liq. ammonia / tetrahydrofuran / 0.5 h / -78 °C

7.1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

With lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; ammonia; iodine; lithium; magnesium; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.2: Crignard reaction;

DOI:10.1016/j.tetasy.2005.08.039

Reference yield:

(2R,3R,4R)-1-O-benzyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3,4-tetrol (869660-96-8) → Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (1053622-69-7)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

2: 550 mg / sodium azide; 18-crown-6 / dimethylsulfoxide / 24 h / 65 °C

3: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

4: 450 mg / triethylamine / tetrahydrofuran / 6 h / 20 °C

5: 83 percent / lithium; liq. ammonia / tetrahydrofuran / 0.5 h / -78 °C

6: triethylamine / CH₂Cl₂ / 1 h / 20 °C

With lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; ammonia; lithium; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tetasy.2005.08.039

upstream raw materials:

(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

methanesulfonyl chloride

1-O-benzyl-2,3-O-isopropylidene-4-oxiranyl-D-arabinitol

(2R,3R,4R)-1-O-benzyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3,4-tetrol

Downstream raw materials:

(2S,3R,4R)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine