(2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl

Base Information

• Chemical Name: (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl
• CAS No.: 180067-21-4
• Molecular Formula: C₃₂H₄₂O₄
• Molecular Weight: 490.683

Synonyms:(2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl

Chemical Property of (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl

There total 32 articles about (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl 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: 68.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (5S,6R)-5-Benzyloxy-6-{(R)-3-[(2S,5R)-5-((R)-1-benzyloxy-pent-4-enyl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-tetrahydro-pyran-2-ol → (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl (180067-21-4)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

(5S,6R)-5-Benzyloxy-6-{(R)-3-[(2S,5R)-5-((R)-1-benzyloxy-pent-4-enyl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-tetrahydro-pyran-2-ol; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(00)00878-4

Reference yield:

D-glucal triacetate (2873-29-2) → (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl (180067-21-4)

Guidance literature:

Multi-step reaction with 16 steps

1.1: BF₃*Et₂O / CH₂Cl₂

2.1: H₂ / Pd/C / ethyl acetate

3.1: NaOMe / methanol

4.1: pyridine

5.1: DEAD; Ph₃P / toluene / -15 - 20 °C

6.1: 5.4 g / NaOMe / methanol / 2 h / 20 °C

7.1: 71 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

8.1: 84 percent / TMEDA / diethyl ether / 8 h / 20 °C

9.1: O₃; O₂ / CH₂Cl₂; methanol / -78 °C

9.2: 80 percent / triphenylphosphine / CH₂Cl₂; methanol / 2 h / -78 - 20 °C

10.1: Na(NSiMe₃)2 / toluene / 1 h / 20 °C

10.2: 84 percent / toluene / 0.75 h / -78 °C

11.1: 100 percent / m-CPBA / aq. phosphate buffer; CH₂Cl₂ / 1 h / 20 °C

12.1: Ph₂PLi / tetrahydrofuran / 2 h

12.2: MeI / 1 h

12.3: 78 percent / n-BuLi

13.1: iodonium dicollidine perchlorate (IDCP) / CH₂Cl₂ / 0.33 h / 20 °C

14.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

14.2: 76 percent / tetrahydrofuran / -78 - 20 °C

15.1: 80 percent / H₂O; BF₃*Et₂O / tetrahydrofuran / 48 h / 20 °C

16.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

16.2: 68 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodonium di(2,4,6-trimethylpyridine) perchlorate; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium methylate; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diphenylphosphide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; 1.1: Ferrier reaction / 2.1: Hydrogenation / 3.1: Deacetylation / 4.1: Tosylation / 5.1: Mitsunobu reaction / 6.1: Hydrolysis / 7.1: Etherification / 8.1: Alkylation / 9.1: ozonolysis / 9.2: Decomposition / 10.1: deprotonation / 10.2: Wittig reaction / 11.1: Epoxidation / 12.1: Ring cleavage / 12.2: inversion / 12.3: Elimination / 13.1: iodoetherification / 14.1: deprotonation / 14.2: Wittig reaction / 15.1: Hydrolysis / 16.1: deprotonation / 16.2: Wittig reaction;

DOI:10.1016/S0040-4020(00)00878-4

Reference yield:

2,2,2-trifluoroethyl?4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (321126-19-6) → (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl (180067-21-4)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 29.3 g / H₂ / Pd/C / ethyl acetate / 16 h

2.1: 18 g / NaOMe / methanol / 2 h / 20 °C

3.1: 84 percent / pyridine / 2.5 h / 20 °C

4.1: 82 percent / NaH; Bu₄NI / tetrahydrofuran / 2 h / 20 °C

5.1: 98 percent / TMEDA / diethyl ether / 8 h / 20 °C

6.1: O₃; O₂ / CH₂Cl₂; methanol / -78 °C

6.2: triphenylphosphine / CH₂Cl₂; methanol / 2 h / -78 - 20 °C

7.1: 6.79 g / NaBH₄ / ethanol / 1 h / 20 °C

8.1: 85 percent / I₂; PPh₃; imidazole / benzene / 1 h / Heating

9.1: 87 percent / diisopropylethylamine / toluene; acetonitrile / 24 h / Heating

10.1: Na(NSiMe₃)2 / toluene / 1 h / 20 °C

10.2: 84 percent / toluene / 0.75 h / -78 °C

11.1: 100 percent / m-CPBA / aq. phosphate buffer; CH₂Cl₂ / 1 h / 20 °C

12.1: Ph₂PLi / tetrahydrofuran / 2 h

12.2: MeI / 1 h

12.3: 78 percent / n-BuLi

13.1: iodonium dicollidine perchlorate (IDCP) / CH₂Cl₂ / 0.33 h / 20 °C

14.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

14.2: 76 percent / tetrahydrofuran / -78 - 20 °C

15.1: 80 percent / H₂O; BF₃*Et₂O / tetrahydrofuran / 48 h / 20 °C

16.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

16.2: 68 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodonium di(2,4,6-trimethylpyridine) perchlorate; boron trifluoride diethyl etherate; water; hydrogen; iodine; oxygen; sodium methylate; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diphenylphosphide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene; 1.1: Hydrogenation / 2.1: Deacetylation / 3.1: Tosylation / 4.1: Etherification / 5.1: Alkylation / 6.1: ozonolysis / 6.2: Decomposition / 7.1: Reduction / 8.1: Iodination / 9.1: Substitution / 10.1: deprotonation / 10.2: Wittig reaction / 11.1: Epoxidation / 12.1: Ring cleavage / 12.2: inversion / 12.3: Elimination / 13.1: iodoetherification / 14.1: deprotonation / 14.2: Wittig reaction / 15.1: Hydrolysis / 16.1: deprotonation / 16.2: Wittig reaction;

DOI:10.1016/S0040-4020(00)00878-4

upstream raw materials:

Methyltriphenylphosphonium bromide

benzyl bromide

tert-butyl 2,3-deoxy-α-D-glucopyranoside

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-tert-butoxy-tetrahydro-pyran-3-yl ester

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