2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

Base Information

• Chemical Name: 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid
• CAS No.: 674336-06-2
• Molecular Formula: C₂₅H₃₀O₆
• Molecular Weight: 426.51

Synonyms:2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

Chemical Property of 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

There total 13 articles about 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid 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: 95.0%

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester (674336-05-1) → 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid (674336-06-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; for 6h; Heating;

DOI:10.1021/ja037957x

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid (674336-06-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / TfOH / diethyl ether / 4 h / 20 °C

2.1: 95 percent / HCl / methanol / 0.17 h / 20 °C

3.1: 93 percent / PCC / CH₂Cl₂ / 4 h

4.1: LHMDS / tetrahydrofuran / -78 - 25 °C

4.2: tetrahydrofuran / 18 h / -78 - 25 °C

5.1: 1.19 g / Hg(OAc)2; aq. KI / tetrahydrofuran; H₂O / 0.5 h

6.1: 75 percent / diethyl ether / 4 h / -78 °C

7.1: 95 percent / aq. LiOH*H₂O / methanol; tetrahydrofuran / 6 h / Heating

With hydrogenchloride; lithium hydroxide; trifluorormethanesulfonic acid; mercury(II) diacetate; pyridinium chlorochromate; potassium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/ja037957x

Reference yield:

2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S)-2-methoxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ylmethyl)-benzoic acid methyl ester → 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid (674336-06-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 74 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

2.1: 70 percent / PPh₃; DIAD / toluene / 16 h / 0 - 25 °C

3.1: 88 percent / 15-crown-5; NaI; BBr₃ / CH₂Cl₂ / 1 h / -30 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 - 20 °C

5.1: 95 percent / K₂CO₃; methanol / 0.17 h / 20 °C

6.1: 93 percent / TfOH / diethyl ether / 4 h / 20 °C

7.1: 95 percent / HCl / methanol / 0.17 h / 20 °C

8.1: 93 percent / PCC / CH₂Cl₂ / 4 h

9.1: LHMDS / tetrahydrofuran / -78 - 25 °C

9.2: tetrahydrofuran / 18 h / -78 - 25 °C

10.1: 1.19 g / Hg(OAc)2; aq. KI / tetrahydrofuran; H₂O / 0.5 h

11.1: 75 percent / diethyl ether / 4 h / -78 °C

12.1: 95 percent / aq. LiOH*H₂O / methanol; tetrahydrofuran / 6 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; methanol; lithium hydroxide; 15-crown-5; trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; mercury(II) diacetate; boron tribromide; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; pyridinium chlorochromate; potassium iodide; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 2.1: Mitsunobu reaction;

DOI:10.1021/ja037957x

upstream raw materials:

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

O-benzyl 2,2,2-trichloroacetimidate

2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S,6R)-4-hydroxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl)-benzoic acid methyl ester

2-((2S,4R,6R)-4-Benzyloxy-6-formyl-tetrahydro-pyran-2-ylmethyl)-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

Downstream raw materials:

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid cyanomethyl ester

((1S,11R,13R,15R)-15-Benzyloxy-7-methoxymethoxy-9-oxo-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-11-yl)-acetaldehyde

(1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 674336-06-2 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

Send

Send

Metric Ton KG G Pound L ML

Send

Send