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

Base Information

• Chemical Name: (1S,2S,4S,5S,6R,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol
• CAS No.: 351884-96-3
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 351884-96-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1S,2S,4S,5S,6R,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol 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,2S,4R,6S,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-one (351884-95-2) → (1S,2S,4S,5S,6R,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-ol (351884-96-3)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; at 0 ℃;

DOI:10.1021/ol015963x

Reference yield:

(1S,5S,7R)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one → (1S,2S,4S,5S,6R,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-ol (351884-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 30percent H₂O₂ / aq. NaOH / pH 13

2: NaBH₄; CeCl₃ / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium hydroxide;

DOI:10.1021/ol015963x

Reference yield:

(1S,2S,4S,5S,6R,7R)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-ol (351884-96-3) → (1R,4R,5S,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol (146830-45-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine

2.1: BF₃*Et₂O / toluene

2.2: 90 percent / NaOMe / methanol

3.1: 99 percent / Huenig base / CH₂Cl₂

4.1: 99 percent / H₂ / Pd/C / ethyl acetate

5.1: 89 percent / I₂; PPh₃; imidazole / tetrahydrofuran

6.1: 98 percent / Zn / acetic acid; methanol / 20 °C

7.1: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C

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

9.1: Grubbs' catalyst / benzene / Heating

10.1: 94 percent / PCC; NaOAc / CH₂Cl₂

11.1: 97 percent / DIBAL / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; quinoline; 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

upstream raw materials:

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

Downstream raw materials:

Benzoic acid (1S,2S,4S,5S,6S,7R)-7-benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]non-5-yl ester

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