(5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Base Information

• Chemical Name: (5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• CAS No.: 121079-15-0
• Molecular Formula: C₂₈H₃₁NO₁₂
• Molecular Weight: 573.554
• Mol file: 121079-15-0.mol

Synonyms:(5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Chemical Property of (5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

There total 2 articles about (5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 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:

5-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-3-methoxy-[1,2]benzoquinone 1-(O-methyl-oxime) → (5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (121079-15-0)

Guidance literature:

With hydrogen; Yield given;

DOI:10.1021/jm00127a002

Reference yield:

etoposide ortho-quinone (105016-65-7) → (5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (121079-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: H₂

With pyridine; hydrogen;

DOI:10.1021/jm00127a002

Reference yield: 79.0%

(5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (121079-15-0) → C28H28N2O12

Guidance literature:

With sodium nitrite; In tetrahydrofuran; acetic acid;

DOI:10.1021/jm00127a002

upstream raw materials:

etoposide ortho-quinone