(4aR)-6t-methoxy-8-methylsulfanyl-2c-phenyl-(4ar,6at,9at,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole

Base Information

• Chemical Name: (4aR)-6t-methoxy-8-methylsulfanyl-2c-phenyl-(4ar,6at,9at,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole
• CAS No.: 69708-60-7
• Molecular Formula: C₁₆H₁₉NO₄S₂
• Molecular Weight: 353.463
• Mol file: 69708-60-7.mol

Synonyms:

Chemical Property of (4aR)-6t-methoxy-8-methylsulfanyl-2c-phenyl-(4ar,6at,9at,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR)-6t-methoxy-8-methylsulfanyl-2c-phenyl-(4ar,6at,9at,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole

There total 5 articles about (4aR)-6t-methoxy-8-methylsulfanyl-2c-phenyl-(4ar,6at,9at,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole 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: 12.0%

methanesulfonyl chloride (124-63-0) + methyl 2-amino-4,6-O-benzylidene-2-deoxy-2-N-<(methylthio)thiocarbonyl>-α-D-altropyranoside (82161-27-1) → 4',6'-O-benzylidene-1'-O-methyl-α-D-mannopyrano<2':3':4,5>-2-methylthio-2-thiazoline (69708-60-7) + methyl-4,6-O-benzylidene-2-deoxy-2-isothiocyano-3-O-methanesulfonyl-α-D-altropyranoside (82161-29-3)

Guidance literature:

In pyridine; for 48h; Ambient temperature;

DOI:10.1002/hlca.19820650205

Reference yield:

methyl O4,O6-(R)-benzylidene-O3-methanesulfonyl-2-methylsulfanylthiocarbonylamino-β-D-2-deoxy-glucopyranoside (107740-08-9) → (4aR)-6t-methoxy-8-methylsulfanyl-2c-phenyl-(4ar,6at,9at,9bt)-4,4a,6,6a,9a,9b-hexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole (69708-60-7)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/S0040-4020(01)99246-4

Reference yield:

methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (6038-60-4) → 4',6'-O-benzylidene-1'-O-methyl-α-D-mannopyrano<2':3':4,5>-2-methylthio-2-thiazoline (69708-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₃N / 1.) pyridine, 0 deg C, 90 min; 2.) pyridine 4 deg C, 14 h

2: 1.) pyridine, 0 deg C, 12 h; 2.) pyridine, 80 deg C, 2.5 h

With triethylamine;

DOI:10.1002/hlca.19820650205

upstream raw materials:

methanesulfonyl chloride

methyl 2-amino-4,6-O-benzylidene-2-deoxy-2-N-<(methylthio)thiocarbonyl>-α-D-altropyranoside

methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside

methyl O⁴,O⁶-(R)-benzylidene-O³-methanesulfonyl-2-methylsulfanylthiocarbonylamino-β-D-2-deoxy-glucopyranoside

Downstream raw materials:

(4aR)-6t-methoxy-2ξ-phenyl-(4ar,6at,9at,9bt)-octahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]thiazole