Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,9-[[4,6-O-(1R)-ethylidene-b-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-,(5R,5aS,8aR,9S)-

Base Information

• Chemical Name: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,9-[[4,6-O-(1R)-ethylidene-b-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-,(5R,5aS,8aR,9S)-
• CAS No.: 100007-56-5
• Molecular Formula: C29H32 O13
• Molecular Weight: 588.565
• Mol file: 100007-56-5.mol

Synonyms:Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,9-[(4,6-O-ethylidene-b-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-,[5R-[5a,5aa,8aa,9b(R*)]]-;Pyrano[3,2-d]-1,3-dioxin, furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-onederiv.; Picro ethylidene lignan P; Picroetoposide; Pptoxin IV; cis-Etoposide

Chemical Property of Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,9-[[4,6-O-(1R)-ethylidene-b-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-,(5R,5aS,8aR,9S)-

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,9-[[4,6-O-(1R)-ethylidene-b-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-,(5R,5aS,8aR,9S)-

There total 9 articles about Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,9-[[4,6-O-(1R)-ethylidene-b-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-,(5R,5aS,8aR,9S)- 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: 87.0%

etoposide (33419-42-0) → picroetoposide (100007-56-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1016/S0040-4020(99)00756-5

Reference yield:

C53H48N6O17 → etoposide (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)

Guidance literature:

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

Reference yield:

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

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

upstream raw materials:

4,6-O-ethylidene-D-glucopyranose

1-O-(trimethylsilyl)-4,6-O-ethylidene-2,3-di-O-(dichloroacetyl)-β-D-glucopyranose

4,6-O-ethylidene-1,2,3-tri-O-(dichloroacetyl)-α-D-glucopyranose

etoposide

Downstream raw materials:

(5R,6S,7R,8S)-8-((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)-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Refernces

• 1、 Meresse, Philippe,Bertounesque, Emmanuel,Imbert, Thierry,Monneret, Claude. "Synthetic approaches to condensed aromatic analogues from etoposide. Synthesis of A-ring pyridazine picroetoposide". . p. 12805 - 12818. Retrieved 2007/10/03.
• 2、 Aso,Yoshioka,Takeda. "Epimerization and racemization of some chiral drugs in the presence of human serum albumin". . p. 180 - 184. Retrieved 2007/10/02.