3β-dihydrocadambine

Base Information

• Chemical Name: 3β-dihydrocadambine
• CAS No.: 61989-80-8
• Molecular Formula: C₂₇H₃₄N₂O₁₀
• Molecular Weight: 546.574
• Mol file: 61989-80-8.mol

Synonyms:

Chemical Property of 3β-dihydrocadambine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-dihydrocadambine

There total 9 articles about 3β-dihydrocadambine 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%

C35H42N2O14 → 3α-dihydrocadambine (54483-84-0,61989-80-8)

Guidance literature:

With potassium carbonate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1002/anie.202005748

Reference yield:

(1R,4aR,8S,8aR)-8-Hydroxymethyl-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester (82958-41-6,82978-48-1) → 3α-dihydro-cadambine (54483-84-0,61989-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: PCC/Celite / sodium acetate / CH₂Cl₂

2: 56 percent / sodium cyanoborohydride

3: 1.) formic acid; 2.) K₂CO₃ / 1.) 95 deg C; 18 h; 2.) methanol

With formic acid; Celite; sodium cyanoborohydride; potassium carbonate; pyridinium chlorochromate; sodium acetate; In dichloromethane;

DOI:10.1016/S0040-4039(00)87341-4

Reference yield:

(4S,5S,6S)-5-((S)-1,2-Dihydroxy-ethyl)-4-(2,2-dimethoxy-ethyl)-6-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (77988-08-0) → 3α-dihydro-cadambine (54483-84-0,61989-80-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Amberlite IR 120 resin / methanol

2: PCC/Celite / sodium acetate / CH₂Cl₂

3: 56 percent / sodium cyanoborohydride

4: 1.) formic acid; 2.) K₂CO₃ / 1.) 95 deg C; 18 h; 2.) methanol

With formic acid; Amberlite IR 120 resin; Celite; sodium cyanoborohydride; potassium carbonate; pyridinium chlorochromate; sodium acetate; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)87341-4

upstream raw materials:

(1R,4aR,8S,8aR)-8-Hydroxymethyl-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester

(1R,4aR,8S,8aR)-8-Formyl-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester

(4S,5S,6S)-5-((S)-1,2-Dihydroxy-ethyl)-4-(2,2-dimethoxy-ethyl)-6-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

(1S,4aS,8S,8aS)-8-{[2-(1H-Indol-3-yl)-ethylamino]-methyl}-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester