(5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide

Base Information

• Chemical Name: (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide
• CAS No.: 1189331-41-6
• Molecular Formula: C₁₁H₁₅NO₄S
• Molecular Weight: 257.31
• Mol file: 1189331-41-6.mol

Synonyms:(5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide

Chemical Property of (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide

There total 4 articles about (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide 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: 28.0%

monochloromethanesulfonyl chloride (3518-65-8) + (2S)-2-amino-3-(benzyloxy)propan-1-ol (58577-88-1) → (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide (1189331-41-6)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃;

Reference yield: 28.0%

(1S)-N-[(2-benzyloxy)-1-(hydroxymethyl)ethyl]chloromethane sulphonamide (1189331-81-4) → (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide (1189331-41-6)

Guidance literature:

With triethylamine; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.09.019

Reference yield:

O-benzyl-D-serine (10433-52-0,32520-12-0) → (5R)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide (1189331-41-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 0 °C / Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

2.2: 0 °C

3.1: triethylamine / dichloromethane / 25 °C

With lithium aluminium tetrahydride; thionyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

monochloromethanesulfonyl chloride

(2S)-2-amino-3-(benzyloxy)propan-1-ol

(1S)-N-[(2-benzyloxy)-1-(hydroxymethyl)ethyl]chloromethane sulphonamide

O-benzyl-D-serine