(3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene

Base Information

• Chemical Name: (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene
• CAS No.: 226885-96-7
• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.454

Synonyms:(3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene

Chemical Property of (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene

Chemical Property:

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Technology Process of (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene

There total 10 articles about (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene 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: 89.0%

N,N-dimethylacetamide dimethyl acetal (18871-66-4) + (3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene (226885-93-4) → (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene (226885-96-7)

Guidance literature:

With 3 A molecular sieve; In xylene; at 140 ℃; for 24h;

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

Reference yield:

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-92-3) → (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene (226885-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.33 h / -78 °C

2: 89 percent / molecular sieves 3 Angstroem / xylene / 24 h / 140 °C

With sodium tetrahydroborate; cerium(III) chloride; 3 A molecular sieve; In methanol; xylene;

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

Reference yield:

(4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-91-2) → (3S,4S,6R)-3-<(N,N-dimethylaminocarbonyl)methyl>-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-cyclohexene (226885-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 24 h / Ambient temperature

2: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.33 h / -78 °C

3: 89 percent / molecular sieves 3 Angstroem / xylene / 24 h / 140 °C

With sodium tetrahydroborate; cerium(III) chloride; 3 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; toluene; xylene;

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

upstream raw materials:

N,N-dimethylacetamide dimethyl acetal

(3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene

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

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

Downstream raw materials:

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

(+)-paniculide A

(1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one

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

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