(4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one

Base Information

• Chemical Name: (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one
• CAS No.: 226885-91-2
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 226885-91-2.mol

Synonyms:(4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one

Chemical Property of (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one

There total 13 articles about (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-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:

(2S,4S)-5-Hydroxy-4-(4-methoxy-benzyloxy)-2-methoxymethoxy-cyclohexanone (748154-80-5) → (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-91-2)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; for 6h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(99)00096-4

Reference yield:

methyl 3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside (226885-88-7) → (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-91-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / I₂; Ph₃P; Imid_. / toluene

2: 91 percent / DIPEA / CH₂Cl₂

3: 100 percent / t-BuOK / tetrahydrofuran

4: Hg(OCOCF₃)2 / acetone; H₂O

5: MsCl; Et₃N / CH₂Cl₂

With 1H-imidazole; potassium tert-butylate; iodine; mercury(II) trifluoroacetate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 4: Ferrier cyclization;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2) → (4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / DIPEA / CH₂Cl₂

2: 100 percent / t-BuOK / tetrahydrofuran

3: Hg(OCOCF₃)2 / acetone; H₂O

4: MsCl; Et₃N / CH₂Cl₂

With potassium tert-butylate; mercury(II) trifluoroacetate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetone; 3: Ferrier cyclization;

DOI:10.1016/j.tetlet.2004.05.129

upstream raw materials:

(2S,4S)-5-Hydroxy-4-(4-methoxy-benzyloxy)-2-methoxymethoxy-cyclohexanone

D-glucose

methyl-alpha-D-glucopyranoside

(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Downstream raw materials:

(6S,7aR)-6-hydroxy-7,7a-dihydrobenzofuran-2(6H)-one

(3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

(3S,3aR,4S,6R,7aR)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

(3S,3aR,4S,6R,7aS)-6-hydroxy-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one