ent-(11S)-3β-methoxy-crin-1-ene-6α,11-diol

Base Information

• Chemical Name: ent-(11S)-3β-methoxy-crin-1-ene-6α,11-diol
• CAS No.: 60944-31-2
• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.342
• Mol file: 60944-31-2.mol

Synonyms:

Chemical Property of ent-(11S)-3β-methoxy-crin-1-ene-6α,11-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ent-(11S)-3β-methoxy-crin-1-ene-6α,11-diol

There total 27 articles about ent-(11S)-3β-methoxy-crin-1-ene-6α,11-diol 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:

2ξ-hydroxy-3c-methoxy-6-oxo-(4ar)-2,3,4,4a,5,6-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridine-11bt-carboxylic acid → rac-(11S)-3α-methoxy-crin-1-ene-6β,11-diol (466-73-9,545-66-4,28405-98-3,33172-28-0,60944-31-2)

Guidance literature:

Multi-step reaction with 6 steps

1: dimethylformamide

2: Py

3: (i) KOH, THF, (ii) SOCl₂

4: K₂CO₃ / dioxane

5: HCl / CH₂Cl₂

6: (i) disiamylborane, (ii) Ac₂O, BF₃-Et₂O, (iii) DABCO, (iv) LiAH₄, THF

With pyridine; hydrogenchloride; potassium carbonate; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00832a027

Reference yield:

2ξ-methanesulfonyloxy-3c-methoxy-6-oxo-(4ar)-2,3,4,4a,5,6-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridine-11bt-carbonyl chloride (54022-44-5) → rac-(11S)-3α-methoxy-crin-1-ene-6β,11-diol (466-73-9,545-66-4,28405-98-3,33172-28-0,60944-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dioxane

2: HCl / CH₂Cl₂

3: (i) disiamylborane, (ii) Ac₂O, BF₃-Et₂O, (iii) DABCO, (iv) LiAH₄, THF

With hydrogenchloride; potassium carbonate; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja00832a027

Reference yield:

2ξ-hydroxy-3c-methoxy-6-oxo-(4ar)-2,3,4,4a,5,6-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridine-11bt-carboxylic acid 2-oxo-2-phenyl-ethyl ester (28406-01-1) → d,l-Haemanthidin (466-73-9,545-66-4,28405-98-3,33172-28-0,60944-31-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / (mesylation)

2: (i) (saponification), (ii) SOCl₂, (iii) /BRN= 102415/

3: HCl

4: (i) disiamylborane, THF, (ii) (acetylation), (iii) DABCO, (iv) LiAlH₄

With hydrogenchloride; In pyridine;

DOI:10.1021/ja00721a053

upstream raw materials:

rac-(11S)-3α,6ξ-dimethoxy-crin-1-en-11-ol

rac-2ξ-methanesulfonyloxy-3α-methoxy-crinane-6,11-dione

3a-benzo[1,3]dioxol-5-yl-6c-methoxy-(3ar,7ac)-octahydro-indole-3t,5t-diol

rac-(11S)-2β,11-diacetoxy-3α,6ξ-dimethoxy-crinane

Downstream raw materials:

pretazettine

tazettine

(4aS)-3t-methoxy-5-methyl-(4ar,13btC¹)-4,4a,5,6-tetrahydro-3H,8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-6at-ol

(4aS)-6a-hydroxy-3t-methoxy-5,5-dimethyl-(4ar,6at,13btC¹)-3,4,4a,5,6,6a-hexahydro-8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indolium; picrate