(1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one

Base Information

• Chemical Name: (1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one
• CAS No.: 351884-95-2
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• Mol file: 351884-95-2.mol

Synonyms:(1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one

Chemical Property of (1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one

There total 1 articles about (1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one 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:

(1S,5S,7R)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one → (1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-one (351884-95-2)

Guidance literature:

With 30percent H₂O₂; sodium hydroxide; pH=13;

DOI:10.1021/ol015963x

Reference yield:

(1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-one (351884-95-2) → conduritol A (526-87-4,351885-26-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaBH₄; CeCl₃ / 0 °C

2.1: pyridine

3.1: BF₃*Et₂O / toluene

3.2: 90 percent / NaOMe / methanol

4.1: 99 percent / Huenig base / CH₂Cl₂

5.1: 99 percent / H₂ / Pd/C / ethyl acetate

6.1: 89 percent / I₂; PPh₃; imidazole / tetrahydrofuran

7.1: 98 percent / Zn / acetic acid; methanol / 20 °C

8.1: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C

9.1: H₂; quinoline / Pd/BaSO₄ / ethyl acetate

10.1: Grubbs' catalyst / benzene / Heating

11.1: 100 percent / satd. HCl / methanol

With pyridine; 1H-imidazole; quinoline; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; hydrogen; iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; toluene; benzene;

DOI:10.1021/ol015963x

Reference yield:

(1S,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-one (351884-95-2) → (1R,2R,3S,4R)-cyclohex-5-ene-1,2,3,4-tetrol (123238-09-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaBH₄; CeCl₃ / 0 °C

2.1: pyridine

3.1: BF₃*Et₂O / toluene

3.2: 90 percent / NaOMe / methanol

4.1: 99 percent / Huenig base / CH₂Cl₂

5.1: 99 percent / H₂ / Pd/C / ethyl acetate

6.1: 89 percent / I₂; PPh₃; imidazole / tetrahydrofuran

7.1: 98 percent / Zn / acetic acid; methanol / 20 °C

8.1: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C

9.1: H₂; quinoline / Pd/BaSO₄ / ethyl acetate

10.1: Grubbs' catalyst / benzene / Heating

11.1: 94 percent / PCC; NaOAc / CH₂Cl₂

12.1: 97 percent / DIBAL / CH₂Cl₂ / -78 °C

13.1: 100 percent / satd. HCl / methanol

With pyridine; 1H-imidazole; quinoline; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; hydrogen; iodine; sodium acetate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; zinc; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; toluene; benzene;

DOI:10.1021/ol015963x

Downstream raw materials:

(1S,2S,4S,5S,6R,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol

conduritol A

(1R,2R,3S,4R)-cyclohex-5-ene-1,2,3,4-tetrol

(1R,4R,5S,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol