(5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Base Information

• Chemical Name: (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• CAS No.: 130370-38-6
• Molecular Formula: C₂₇H₃₀O₁₂S
• Molecular Weight: 578.594

Synonyms:(5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Chemical Property of (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-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):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

There total 5 articles about (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-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: 70.0%

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(5S,5aR,8aR)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-ylsulfanyl]-tetrahydro-pyran-3-yl ester (139111-06-1) → (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (130370-38-6)

Guidance literature:

With zinc diacetate; In methanol; for 40h; Heating;

DOI:10.1016/0040-4039(91)80446-D

Reference yield:

tetraacetyl thioglucose (19879-84-6) → (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (130370-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 25 °C

2: 70 percent / Zn(OAc)2 / methanol / 40 h / Heating

With boron trifluoride diethyl etherate; zinc diacetate; In methanol; dichloromethane;

DOI:10.1016/0040-4039(91)80446-D

Reference yield:

4’-demethylepipodophyllotoxin (6559-91-7,40505-27-9,77519-36-9,87584-72-3,96554-39-1,104264-48-4,107079-65-2,112066-16-7,112246-55-6) → (5aR,8aR,9S)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (130370-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 25 °C

2: 70 percent / Zn(OAc)2 / methanol / 40 h / Heating

With boron trifluoride diethyl etherate; zinc diacetate; In methanol; dichloromethane;

DOI:10.1016/0040-4039(91)80446-D

upstream raw materials:

4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin

sodium salt of 1-thio-α-D-glucopyranose

4-demethylpodophyllotoxin

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(5S,5aR,8aR)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-ylsulfanyl]-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(5R,5aR,8aR,9S)-9-((2R,4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl)-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

(5R,5aR,8aR,9S)-9-((2R,4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl)-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

C₃₅H₃₅Cl₃O₁₅S

C₃₅H₃₅Cl₃O₁₇S

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