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

Base Information

Chemical Name:(5S,5aS,8aS,9R)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
CAS No.:112246-48-7
Molecular Formula:C₂₉H₃₂O₁₃
Molecular Weight:588.565
Hs Code.:

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

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

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

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

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

There total 12 articles about (5S,5aS,8aS,9R)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-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:

: 92206-84-3
2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopuranose

: 92206-82-1,112246-47-6
Chloro-acetic acid 4-((5S,5aS,9R)-9-hydroxy-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester

: 33419-42-0
etoposide

: 112246-48-7
(5S,5aS,8aS,9R)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Guidance literature:: With boron trifluoride diethyl etherate; zinc diacetate; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, 2.) reflux, MeOH;
DOI:10.1246/cl.1987.799

Reference yield:

: C₅₃H₄₈N₆O₁₇

: 33419-42-0,89301-95-1,96554-38-0,96554-41-5,100007-53-2,100007-56-5,112246-48-7,112246-49-8,112246-50-1,132880-83-2,134623-79-3,136232-35-4,136232-37-6,136232-38-7,140223-11-6
etoposide

Guidance literature:: With palladium 10% on activated carbon; In 1,4-dioxane; methanol; at 30 ℃; for 4h; Inert atmosphere; Green chemistry;

Reference yield:

: 18465-50-4,13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,87068-63-1
4,6-O-ethylidene-D-glucopyranose

: 33419-42-0,89301-95-1,96554-38-0,96554-41-5,100007-53-2,100007-56-5,112246-48-7,112246-49-8,112246-50-1,132880-83-2,134623-79-3,136232-35-4,136232-37-6,136232-38-7,140223-11-6
etoposide

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 2 h / 0 °C

2: MeOH / CH₂Cl₂ / 20 h / 20 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: BF₃*Et₂O / CH₂Cl₂ / 1) -20 deg C, 8 h, 2) -10 deg C, 30 min

5: MeOH, zinc acetate dihydrate / 1.5 h / Heating

With pyridine; methanol; boron trifluoride diethyl etherate; zinc diacetate; triethylamine; In dichloromethane;
DOI:10.1021/jo00067a071