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

Base Information

• Chemical Name: (3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene
• CAS No.: 226885-93-4
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 226885-93-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(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: 86.0%

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-92-3) → (3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene (226885-93-4) + (3R,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 0.333333h;

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,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene (226885-93-4)

Guidance literature:

Multi-step reaction with 2 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

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

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

Reference yield:

(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2) → (3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene (226885-93-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / diisopropylethylamine / CH₂Cl₂ / 96 h / Ambient temperature

2: 85 percent / potassium t-butoxide / tetrahydrofuran / 3.5 h / Ambient temperature

3: mercury(II) trifluoroacetate / H₂O / 24 h / Ambient temperature

4: MsCl, Et₃N / CH₂Cl₂ / 6 h / Ambient temperature

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 24 h / Ambient temperature

6: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.33 h / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; potassium tert-butylate; mercury(II) trifluoroacetate; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

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

upstream raw materials:

(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

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

methyl 3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside

Downstream raw materials:

(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

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