(3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene

Base Information

• Chemical Name: (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene
• CAS No.: 210764-96-8
• Molecular Formula: C₂₇H₃₄O₆
• Molecular Weight: 454.563

Synonyms:(3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene

Chemical Property of (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene

There total 11 articles about (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene 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: 71.0%

Dithiocarbonic acid O-[(1R,2S,5S,6R)-5,6-bis-(4-methoxy-benzyloxy)-2-(tetrahydro-pyran-2-yloxy)-cyclohex-3-enyl] ester S-methyl ester (222545-17-7) → (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene (210764-96-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 15h; Heating;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5) → (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene (210764-96-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

2: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

3: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

4: 1.) NaH, imidazole / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1.5 h, 3.) 0 deg C, 30 min

5: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; In methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

methyl 4-O-acetyl-2,3-di-O-(4-methoxy)benzyl-α-D-xylo-hex-5-enopyranoside (210764-92-4) → (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene (210764-96-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

2: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

3: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

4: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

5: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

6: 1.) NaH, imidazole / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1.5 h, 3.) 0 deg C, 30 min

7: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; methanesulfonyl chloride; In methanol; dichloromethane; water; acetone; toluene;

DOI:10.1016/S0040-4020(99)00004-6

upstream raw materials:

Dithiocarbonic acid O-[(1R,2S,5S,6R)-5,6-bis-(4-methoxy-benzyloxy)-2-(tetrahydro-pyran-2-yloxy)-cyclohex-3-enyl] ester S-methyl ester

p-methoxybenzyl chloride

methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside

methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside

Downstream raw materials:

(1R,2R,3S,4S)-2-<(1R)-1-methylprop-2-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

(3S,3aR,4S,5S,7aR)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-octahydro-benzofuran-2-ol

(3S,3aS,4S,5S,7aR)-4,5-di-(4-methoxybenzyl)oxy-3-methyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

2-[(1S,5S,6S)-5,6-Bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl]-propionic acid

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