9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester
• CAS No.: 194603-23-1
• Molecular Formula: C₂₇H₃₉NO₉
• Molecular Weight: 521.608
• Mol file: 194603-23-1.mol

Synonyms:9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester

Chemical Property of 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester

There total 4 articles about 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl 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: 95.0%

benzaldehyde dimethyl acetal (1125-88-8) + 9-((2R,3R,4R,5S,6R)-3-Allyloxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-nonanoic acid methyl ester (177610-00-3) → 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester (194603-23-1)

Guidance literature:

With camphor-10-sulfonic acid; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/S0008-6215(98)00229-8

Reference yield:

methyl 9-hydroxynonanoate (34957-73-8) → 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester (194603-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / trimethylsilyl triflate / -35 °C

2: 100 percent / NaOMe / methanol

3: 88 percent / PTSA / acetonitrile

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1016/S0960-894X(01)00092-0

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose (112929-24-5,112929-25-6) → 9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester (194603-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / trimethylsilyl triflate / -35 °C

2: 100 percent / NaOMe / methanol

3: 88 percent / PTSA / acetonitrile

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1016/S0960-894X(01)00092-0

upstream raw materials:

benzaldehyde dimethyl acetal

9-((2R,3R,4R,5S,6R)-3-Allyloxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-nonanoic acid methyl ester

methyl 9-hydroxynonanoate

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose

Downstream raw materials:

9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

9-[(2R,3R,4R,5S,6R)-3-Allyloxycarbonylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

9-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

9-[(2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-nonanoic acid methyl ester