(1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone

Base Information

• Chemical Name: (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone
• CAS No.: 1198791-02-4
• Molecular Formula: C₂₉H₄₄O₅S₂Si₂
• Molecular Weight: 592.968
• Mol file: 1198791-02-4.mol

Synonyms:(1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone

Chemical Property of (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone

There total 1 articles about (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone 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: 35.0%

(1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone (862791-12-6) + 2-thenyl bromide (45438-73-1) → (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxycyclohex-2-en-1,5-carbolactone (1198791-01-3) + (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone (1198791-02-4)

Guidance literature:

(1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone; With potassium hexamethylsilazane; In N,N-dimethyl-formamide; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

2-thenyl bromide; In N,N-dimethyl-formamide; toluene; for 0.75h; Inert atmosphere;

DOI:10.1021/jm9010466

Reference yield:

(1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone (1198791-02-4) → sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-ene-1-carboxylate (1233376-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

2: sodium hydroxide / tetrahydrofuran; water / 0.25 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/jm2006063

Reference yield:

(1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone (1198791-02-4) → methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate (1319745-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

2: methanol / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1021/jm2006063

upstream raw materials:

(1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone

2-thenyl bromide

Downstream raw materials:

sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-ene-1-carboxylate

methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate