(+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt

Base Information

• Chemical Name: (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt
• CAS No.: 102917-72-6
• Molecular Formula: C₈H₁₁N*C₁₁H₁₆O₅
• Molecular Weight: 349.427
• Mol file: 102917-72-6.mol

Synonyms:(+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt

Chemical Property of (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt

There total 1 articles about (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt 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:

(S)-1-phenyl-ethylamine (2627-86-3) + (1S*,2R*,3R*,5R*)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid (71923-86-9,87727-16-0,91603-54-2,102917-73-7) → (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt (102917-72-6)

Guidance literature:

In chloroform; at 5 ℃;

DOI:10.1248/cpb.33.2688

Reference yield:

(+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt (102917-72-6) → (-)-(1S,2S,3R,5R)-3-(tetrahydropyran-2-yl)oxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-methanol (70871-22-6,71773-27-8,89888-64-2,91603-55-3,99266-32-7,102491-15-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 12.4 g / diethyl ether

2: 16.7 g / picric acid / benzene / 2.25 h / Ambient temperature

3: 14.8 g / LiAlH₄ / diethyl ether / 1.17 h / Ambient temperature

With lithium aluminium tetrahydride; 2,4,6-Trinitrophenol; In diethyl ether; benzene;

DOI:10.1248/cpb.33.2688

Reference yield:

(+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt (102917-72-6) → (5E)-carba-PGI2 (69552-46-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 12.4 g / diethyl ether

2: 16.7 g / picric acid / benzene / 2.25 h / Ambient temperature

3: 14.8 g / LiAlH₄ / diethyl ether / 1.17 h / Ambient temperature

4: 1.) pyridine-SO₃/Et₃N / 1.) DMSO, room temp., 30 min; 2.) ether, 2 h, room temp.

5: 2.64 g / NaBH₄ / methanol / 1.5 h / 0 °C

6: 789 mg / conc. HCl / H₂O; acetone / 3.25 h / 3 °C

7: 184 mg / p-TsOH / CH₂Cl₂ / 0.75 h / 0 °C

8: sodium methylsulfinylmethide / dimethylsulfoxide / 30 h / Ambient temperature

9: 97 mg / diethyl ether

10: 514 mg / aq. acetic acid / 24 h / 30 - 40 °C

11: 188 mg / pyridine / 3 °C

12: 216 mg / 5percent KOH / methanol; H₂O / 2 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dimsylsodium; sulfur trioxide pyridine complex; triethylamine; 2,4,6-Trinitrophenol; toluene-4-sulfonic acid; In pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; acetone; benzene;

DOI:10.1248/cpb.33.2688

upstream raw materials:

(S)-1-phenyl-ethylamine

(1S^*,2R^*,3R^*,5R^*)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid

Downstream raw materials:

carbacyclin

(5E)-carba-PGI2

(-)-(1S,2S,3R,5R)-3-(tetrahydropyran-2-yl)oxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-methanol