6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide

Base Information

• Chemical Name: 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide
• CAS No.: 124781-20-0
• Molecular Formula: C₃₁H₄₄O₈
• Molecular Weight: 544.686
• Mol file: 124781-20-0.mol

Synonyms:6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide

Chemical Property of 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide

There total 9 articles about 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide 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: 57.0%

4-formyl-1(R)-methyl-3(E)-butenyl (3R,4S,5S,6R,8R)-10-dimethoxyphosphono-3,5-isopropylidenedioxy-4-methoxy-6-<2-(4-methoxybenzyloxy)ethyl>-8-methyl-9-oxodecanoate (129251-01-0) → 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide (124781-20-0)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; for 17h; Ambient temperature;

Reference yield:

(S)-2,2-Diethyl-4-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-[1,3]dioxolane (133839-50-6) → 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide (124781-20-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / 2percent H₂SO₄ / methanol / 4 h / Ambient temperature

2: 72 percent / pyridine / CH₂Cl₂ / 10 h / Ambient temperature

3: 92 percent / LiAlH₄ / diethyl ether / 0.67 h / 0 °C

4: 90 percent / DDQ, H₂O / CH₂Cl₂ / 0.67 h

5: 90 percent / active MnO₂ / CH₂Cl₂ / 1 h

6: 1) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2) DMAP / 1) THF, r.t, 1h, 2) toluene, 1.5h

7: 57 percent / 18-crown-6, K₂CO₃ / toluene / 17 h / Ambient temperature

With pyridine; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; 18-crown-6 ether; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; water; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1248/cpb.39.64

Reference yield:

(-)-(5R)-hydroxy-(2E)-hexenal (69830-85-9) → 6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide (124781-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2) DMAP / 1) THF, r.t, 1h, 2) toluene, 1.5h

2: 57 percent / 18-crown-6, K₂CO₃ / toluene / 17 h / Ambient temperature

With dmap; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; potassium carbonate; triethylamine; In toluene;

DOI:10.1248/cpb.39.64

upstream raw materials:

4-formyl-1(R)-methyl-3(E)-butenyl (3R,4S,5S,6R,8R)-10-dimethoxyphosphono-3,5-isopropylidenedioxy-4-methoxy-6-<2-(4-methoxybenzyloxy)ethyl>-8-methyl-9-oxodecanoate

(-)-(5R)-hydroxy-(2E)-hexenal

(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

(S)-2,2-Diethyl-4-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-[1,3]dioxolane

Downstream raw materials:

6''-dihydro-3,5-isopropylidene-6''-O-(4-methoxybenzyl) leuconolide A₁

(E)-(1R,5R,7R,9S,13R,15R,16S,20S)-20-Methoxy-15-[2-(4-methoxy-benzyloxy)-ethyl]-5,13,18,18-tetramethyl-4,8,17,19-tetraoxa-tricyclo[14.3.1.0^7,9]icos-10-ene-3,12-dione

6''-dihydro-6''-O-(4-methoxybenzyl)niddanolide

(E)-(1R,5R,7R,9S,12R,13R,15R,16S,20S)-12-Hydroxy-20-methoxy-15-[2-(4-methoxy-benzyloxy)-ethyl]-5,13,18,18-tetramethyl-4,8,17,19-tetraoxa-tricyclo[14.3.1.0^7,9]icos-10-en-3-one