((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester

Base Information

• Chemical Name: ((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester
• CAS No.: 182865-71-0
• Molecular Formula: C₁₉H₂₅NO₇
• Molecular Weight: 379.41
• Mol file: 182865-71-0.mol

Synonyms:((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester

Chemical Property of ((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester

There total 2 articles about ((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl 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: 100.0%

benzaldehyde dimethyl acetal (1125-88-8) + ((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester (182865-98-1) → ((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester (182865-71-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1016/0960-894X(96)00370-8

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose (112929-24-5,112929-25-6) → ((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester (182865-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / TMSOTf, MS₄A / 1,2-dichloro-ethane

2: 98 percent / NaOMe / methanol

3: 100 percent / p-TosOH / acetonitrile

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/0960-894X(96)00370-8

Reference yield:

((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester (182865-71-0) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (182865-85-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / Hg(CN)2, HgBr₂, MS₄A / 1,2-dichloro-ethane

2: 73 percent / NaBH₃CN, TMSCl / tetrahydrofuran / 0 deg C -> room temperature

3: 80 percent / TMSOTf / diethyl ether; tetrahydrofuran

4: 94 percent / Pd(PPh₃)4, polymethylhydrosiloxane / tetrahydrofuran

5: 87 percent / DMAP, pyridine

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; polymethylhydrosiloxane; trimethylsilyl trifluoromethanesulfonate; mercury(II) cyanide; sodium cyanoborohydride; mercury dibromide; In tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane;

DOI:10.1016/0960-894X(96)00370-8

upstream raw materials:

benzaldehyde dimethyl acetal

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester

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

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6R)-3-allyloxycarbonylamino-6-benzyloxymethyl-2-ethoxy-5-hydroxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-amino-2-benzyloxymethyl-6-ethoxy-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-amino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester