(R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester

Base Information

• Chemical Name: (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester
• CAS No.: 866890-52-0
• Molecular Formula: C₃₁H₄₁NO₁₃
• Molecular Weight: 635.665

Synonyms:

Chemical Property of (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester

There total 6 articles about (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl 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:

methyl {2,4,6-tri-O-acetyl-3-O-[(R)-1-(benzyloxycarbonyl)-2-phenylethyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranoside (866890-44-0) → (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester (866890-52-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 12h;

DOI:10.1080/07328300500176312

Reference yield:

(3aR,4R,5aR,8S,9aS,9bS)-4-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2,2-dibutyl-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene → (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester (866890-52-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 mg / CsF / 1,2-dimethoxy-ethane / 2 h / 20 °C

2.1: 1,3-propanedithiol; pyridine; triethylamine / H₂O / 4 h / 20 °C / pH 9 - 10

3.1: 36 mg / pyridine / 19 h / 20 °C

4.1: ethanethiol; TsOH / CH₂Cl₂; methanol / 4 h / 20 °C

4.2: 69 percent / pyridine / 72 h / 20 °C

5.1: sodium methanolate / methanol / 12 h / 20 °C

With pyridine; 1.3-propanedithiol; sodium methylate; toluene-4-sulfonic acid; triethylamine; cesium fluoride; ethanethiol; In methanol; 1,2-dimethoxyethane; dichloromethane; water; 5.1: Zemplen deacetylation;

DOI:10.1080/07328300500176312

Reference yield:

(R)-2-[(2S,4aR,6R,7R,8R,8aS)-6-((2S,4aR,6R,7R,8R,8aR)-7-Amino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3-phenyl-propionic acid benzyl ester → (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester (866890-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 36 mg / pyridine / 19 h / 20 °C

2.1: ethanethiol; TsOH / CH₂Cl₂; methanol / 4 h / 20 °C

2.2: 69 percent / pyridine / 72 h / 20 °C

3.1: sodium methanolate / methanol / 12 h / 20 °C

With pyridine; sodium methylate; toluene-4-sulfonic acid; ethanethiol; In methanol; dichloromethane; 3.1: Zemplen deacetylation;

DOI:10.1080/07328300500176312

upstream raw materials:

methyl {2,4,6-tri-O-acetyl-3-O-[(R)-1-(benzyloxycarbonyl)-2-phenylethyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranoside

methyl {4,6-O-benzylidene-3-O-[(R)-1-(benzyloxycarbonyl)-2-phenylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

methyl {2-O-acetyl-4,6-O-benzylidene-3-O-[(R)-1-(benzyloxycarbonyl)-2-phenylethyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester

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