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

Base Information Edit

Chemical Name:(1S,4R,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol
CAS No.:266693-94-1
Molecular Formula:C₁₂H₂₂O₇
Molecular Weight:278.302
Hs Code.:
Mol file:266693-94-1.mol

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

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

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

There total 18 articles about (1S,4R,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: 77.0%

: 266693-93-0
(1S,4R,4aS,5S,6R,7R,8R,8aR)-6,7,8-Tris-methoxymethoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol

: 266693-94-1
(1S,4R,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol

Guidance literature:: With sodium hydrogencarbonate; In diphenylether; for 0.5h; Heating;
DOI:10.1039/a905462f

Reference yield:

: 243987-96-4
(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol

: 266693-94-1
(1S,4R,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 9 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: 61 percent / LDA / tetrahydrofuran / -78 - 20 °C

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

9: Grubbs' catalyst / benzene / Heating

With 1H-imidazole; quinoline; osmium(VIII) oxide; N-methyl-2-indolinone; 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; 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

: 266693-94-1
(1S,4R,5R,6R)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 10 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: 61 percent / LDA / tetrahydrofuran / -78 - 20 °C

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

10: Grubbs' catalyst / benzene / Heating

With 1H-imidazole; quinoline; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; 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; water; acetic acid; ethyl acetate; benzene;
DOI:10.1021/ol015963x