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

Base Information

• Chemical Name: (1S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol
• CAS No.: 351885-24-0
• Molecular Formula: C₁₂H₂₂O₇
• Molecular Weight: 278.302
• Mol file: 351885-24-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about (1S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol 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: 93.0%

(4S,5R,6S)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enone (266693-96-3) → (1S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol (351885-24-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride;

DOI:10.1039/a905462f

Reference yield:

(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol (243987-96-4) → (1S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol (351885-24-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 94 percent / Huenig base / CH₂Cl₂

2: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O

3: 95 percent / Huenig base / CH₂Cl₂

4: 93 percent / H₂ / Pd/C / ethyl acetate

5: 90 percent / I₂; PPh₃; imidazole / tetrahydrofuran

6: 96 percent / Zn / acetic acid; methanol / 20 °C

7: 88 percent / TPAP; NMO / CH₂Cl₂

8: 44 percent / DABCO / benzene / Heating

9: 93 percent / DIBAL / CH₂Cl₂ / -78 °C

10: 61 percent / LDA / tetrahydrofuran / -78 - 20 °C

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

12: Grubbs' catalyst / benzene / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; quinoline; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydrogen; iodine; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; benzene;

DOI:10.1021/ol015963x

Reference yield:

(1S,5S,7R)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one → (1S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol (351885-24-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 90 percent / NaBH₄; CeCl₃ / 0 °C

2: 94 percent / Huenig base / CH₂Cl₂

3: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O

4: 95 percent / Huenig base / CH₂Cl₂

5: 93 percent / H₂ / Pd/C / ethyl acetate

6: 90 percent / I₂; PPh₃; imidazole / tetrahydrofuran

7: 96 percent / Zn / acetic acid; methanol / 20 °C

8: 88 percent / TPAP; NMO / CH₂Cl₂

9: 44 percent / DABCO / benzene / Heating

10: 93 percent / DIBAL / CH₂Cl₂ / -78 °C

11: 61 percent / LDA / tetrahydrofuran / -78 - 20 °C

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

13: Grubbs' catalyst / benzene / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; quinoline; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; hydrogen; iodine; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; benzene;

DOI:10.1021/ol015963x

upstream raw materials:

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

(3S,4R,5R,6S)-4,5,6-Tris-methoxymethoxy-octa-1,7-dien-3-ol

(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol

(1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene

Downstream raw materials:

(1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene