Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate

Base Information

• Chemical Name: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate
• CAS No.: 793695-59-7
• Molecular Formula: C12H18O5
• Molecular Weight: 242.272
• Mol file: 793695-59-7.mol

Synonyms:Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate;

Chemical Property of Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate

Chemical Property:

• PSA: 64.99000
• LogP: 0.45040

Purity/Quality:

99% ^*data from raw suppliers

Ethyl(1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate is used in the synthesis of A3 adenosine receptor agonists and antagonists.

Technology Process of Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate

There total 12 articles about Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate 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: 55.0%

ethyl (1S,2R,3R,4S,5S)-3,4-O-isopropylidene-2-hydroxybicyclo[3.1.0]hexane-1-carboxylate (828935-09-7) → ethyl (1S,2R,3S,4S,5S)-2,3-O-isopropylidene-4-hydroxybicyclo[3.1.0]hexane-1-carboxylate (793695-59-7)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 25 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jm9018542

Reference yield:

(4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde (116669-78-4) → ethyl (1S,2R,3S,4S,5S)-2,3-O-isopropylidene-4-hydroxybicyclo[3.1.0]hexane-1-carboxylate (793695-59-7)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOCl

2: tetrahydrofuran / 0 - 30 °C

3: 0.293 g / tetrahydrofuran / -78 °C

4: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

5: 41 percent / TsOH*H₂O / acetone / 8 h / Heating

With sodium hypochlorite; sodium tetrahydroborate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone; 3: Dieckmann condensation;

DOI:10.1021/jo0487606

Reference yield:

ethyl (4S,5S)-3-[2,2-dimethyl-5-vinyl(1,3-dioxolan-4-yl)]-3-oxopropanoate (495397-63-2) → ethyl (1S,2R,3S,4S,5S)-2,3-O-isopropylidene-4-hydroxybicyclo[3.1.0]hexane-1-carboxylate (793695-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

2: 41 percent / TsOH*H₂O / acetone / 8 h / Heating

With sodium tetrahydroborate; toluene-4-sulfonic acid; In methanol; acetone;

DOI:10.1021/jo0487606

upstream raw materials:

ethyl (1S,2R,3R,4S,5S)-3,4-O-isopropylidene-2-hydroxybicyclo[3.1.0]hexane-1-carboxylate

D-erythronolactone acetonide

2,3-O-isopropylidene-D-erythrose

(4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol

Downstream raw materials:

(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol

Refernces

• 1、 -. "COMPOUNDS TARGETING PRMT5". Paragraph 0161; 0168. . Retrieved 2020/10/20.
• 2、 Santhosh Kumar,Zhou, Si-Yuan,Joshi, Bhalchandra V.,Balasubramanian, Ramachandran,Yang, Tiehong,Liang, Bruce T.,Jacobson, Kenneth A.. "Structure-activity relationship of (N)-methanocarba phosphonate analogues of 5′-AMP as cardioprotective agents acting through a cardiac P2X receptor". supporting information; experimental part. p. 2562 - 2576. Retrieved 2010/08/19.