(4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester

Base Information

• Chemical Name: (4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester
• CAS No.: 1332628-41-7
• Molecular Formula: C₂₈H₃₁NO₆
• Molecular Weight: 477.557
• Mol file: 1332628-41-7.mol

Synonyms:(4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester

Chemical Property of (4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester

There total 1 articles about (4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-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: 79.0%

N-(methoxy(phenyl)methyl)benzamide (10387-93-6) + 3,4-di-O-(2-propenyl)-6-O-acetyl-D-galactal (1332628-23-5) → (4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester (1332628-41-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol2019604

Reference yield: 94.0%

methanol (67-56-1) + (4S,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester (1332628-41-7) → (2R,3R,4R,5S)-acetic acid 3,4-bis-allyloxy-5-(benzoylamino-phenyl-methyl)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (1332628-53-1)

Guidance literature:

at 80 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol2019604

upstream raw materials:

N-(methoxy(phenyl)methyl)benzamide

3,4-di-O-(2-propenyl)-6-O-acetyl-D-galactal

Downstream raw materials:

(2R,3R,4R,5S)-acetic acid 3,4-bis-allyloxy-5-(benzoylamino-phenyl-methyl)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester