(5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester
• CAS No.: 620116-60-1
• Molecular Formula: C₂₃H₂₆O₉
• Molecular Weight: 446.454
• Mol file: 620116-60-1.mol

Synonyms:(5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Chemical Property of (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

There total 6 articles about (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl 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:

(5S,6S,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester (620116-48-5) → (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester (620116-60-1)

Guidance literature:

(5S,6S,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 25 ℃; for 6h;

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 1h;

With silica gel; In methanol; at 56 ℃; for 2h;

DOI:10.1021/ja0376588

Reference yield:

[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol (620116-45-2) → (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester (620116-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / pyridine / CH₂Cl₂ / 2.5 h / 25 °C

2.1: 38 percent / tris(trimethylsilyl)silane; AIBN / benzene / 6 h / 80 °C

3.1: 96 percent / n-Bu₄NF; AcOH / tetrahydrofuran / 8 h / 25 °C

4.1: 100 percent / PCC / CH₂Cl₂ / 5 h / 25 °C

5.1: 89 percent / H₂SO₄ / 2 h / 25 °C

6.1: DBU / tetrahydrofuran / 6 h / 25 °C

6.2: LiEt₃BH / tetrahydrofuran / 1 h / -78 °C

6.3: SiO₂ / methanol / 2 h / 56 °C

With pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; sulfuric acid; tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja0376588

Reference yield:

(+)-isopicropodophyllone (620116-42-9) → (5S,6S,7S,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester (620116-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / H₂SO₄ / 2 h / 25 °C

2.1: DBU / tetrahydrofuran / 6 h / 25 °C

2.2: LiEt₃BH / tetrahydrofuran / 1 h / -78 °C

2.3: SiO₂ / methanol / 2 h / 56 °C

With sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1021/ja0376588

upstream raw materials:

(5S,6S,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol

(+)-isopicropodophyllone

podophyllotoxin