(5S,6S,7S,8S)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Base Information

• Chemical Name: (5S,6S,7S,8S)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid
• CAS No.: 104715-48-2
• Molecular Formula: C₂₂H₂₅NO₈
• Molecular Weight: 431.442
• Mol file: 104715-48-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (5S,6S,7S,8S)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 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:

(2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (88775-47-7) → (5S,6S,7S,8R)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (104715-48-2,106137-42-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent

2: 95 percent / BF₃*Et₂O, Ac₂O / nitromethane / 1 h / Ambient temperature

3: 5percent KOH / methanol

4: NaBH₄ / ethanol; CH₂Cl₂; H₂O / 40 °C

5: TsOH / toluene / Heating

6: TsOH / toluene / Heating

7: 94 percent / LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C

8: 65 percent / KHCO₃ / ethyl acetate / Heating

9: 75 percent / 1N HCl, CH₃COCl / methanol; nitromethane / Ambient temperature

10: 90 percent / H₂ / RaNi / methanol; H₂O; CH₂Cl₂ / 6 h / 2068.6 Torr

11: lithium aluminium hydride / tetrahydrofuran / 16 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetyl chloride; lithium diisopropyl amide; RaNi; In tetrahydrofuran; methanol; nitromethane; ethanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(00)84725-5

Reference yield:

(5R,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (106044-42-2,107344-08-1) → (5S,6S,7S,8R)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (104715-48-2,106137-42-2)

Guidance literature:

Multi-step reaction with 6 steps

1: TsOH / toluene / Heating

2: 94 percent / LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C

3: 65 percent / KHCO₃ / ethyl acetate / Heating

4: 75 percent / 1N HCl, CH₃COCl / methanol; nitromethane / Ambient temperature

5: 90 percent / H₂ / RaNi / methanol; H₂O; CH₂Cl₂ / 6 h / 2068.6 Torr

6: lithium aluminium hydride / tetrahydrofuran / 16 h / Ambient temperature

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetyl chloride; lithium diisopropyl amide; RaNi; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(00)84725-5

Reference yield:

(5R,6R)-8-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (100146-47-2) → (5S,6S,7S,8R)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (104715-48-2,106137-42-2)

Guidance literature:

Multi-step reaction with 7 steps

1: TsOH / toluene / Heating

2: TsOH / toluene / Heating

3: 94 percent / LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C

4: 65 percent / KHCO₃ / ethyl acetate / Heating

5: 75 percent / 1N HCl, CH₃COCl / methanol; nitromethane / Ambient temperature

6: 90 percent / H₂ / RaNi / methanol; H₂O; CH₂Cl₂ / 6 h / 2068.6 Torr

7: lithium aluminium hydride / tetrahydrofuran / 16 h / Ambient temperature

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetyl chloride; lithium diisopropyl amide; RaNi; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(00)84725-5

upstream raw materials:

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

(2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

(5R,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

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

Downstream raw materials:

9-hydroxy-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

(+/-) epipodophyllotoxin

Refernces

• 1、 Macdonald,Durst. "A highly stereoselective Diels-Alder based synthesis of (±)-podophyllotoxin". . p. 4749 - 4750. Retrieved 2007/10/02.