thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester

Base Information

• Chemical Name: thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester
• CAS No.: 620116-46-3
• Molecular Formula: C₂₈H₃₆O₈SSi
• Molecular Weight: 560.741
• Mol file: 620116-46-3.mol

Synonyms:thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester

Chemical Property of thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester

There total 2 articles about thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) 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:

(R)-2-[(S)-(tert-Butyl-dimethyl-silanyloxy)-(6-vinyl-benzo[1,3]dioxol-5-yl)-methyl]-but-3-en-1-ol (620116-44-1) → thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester (620116-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Grubbs catalyst / CH₂Cl₂ / 2 h / 25 °C

2: 89 percent / pyridine / CH₂Cl₂ / 2.5 h / 25 °C

With pyridine; Grubbs catalyst first generation; In dichloromethane;

DOI:10.1021/ja0376588

Reference yield:

(S)-4-Benzyl-3-{(S)-2-[(S)-(tert-butyl-dimethyl-silanyloxy)-(6-vinyl-benzo[1,3]dioxol-5-yl)-methyl]-but-3-enoyl}-oxazolidin-2-one (620116-43-0) → thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester (620116-46-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 25 °C

2: 91 percent / Grubbs catalyst / CH₂Cl₂ / 2 h / 25 °C

3: 89 percent / pyridine / CH₂Cl₂ / 2.5 h / 25 °C

With pyridine; sodium tetrahydroborate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja0376588

Reference yield: 38.0%

thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester (620116-46-3) → 9-(tert-butyl-dimethyl-silanyloxy)-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (620116-47-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In benzene; at 80 ℃; for 6h;

DOI:10.1021/ja0376588

upstream raw materials:

(R)-2-[(S)-(tert-Butyl-dimethyl-silanyloxy)-(6-vinyl-benzo[1,3]dioxol-5-yl)-methyl]-but-3-en-1-ol

(S)-4-Benzyl-3-{(S)-2-[(S)-(tert-butyl-dimethyl-silanyloxy)-(6-vinyl-benzo[1,3]dioxol-5-yl)-methyl]-but-3-enoyl}-oxazolidin-2-one

Downstream raw materials:

9-(tert-butyl-dimethyl-silanyloxy)-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

(1α,2α,3α)-podophyllotoxin

(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

(+)-isopicropodophyllone