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

Base Information

• Chemical Name: 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
• CAS No.: 222545-17-7
• Molecular Formula: C₂₉H₃₆O₇S₂
• Molecular Weight: 560.733

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 9 articles about 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 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:

(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5) → 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)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; In methanol; dichloromethane;

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) → 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)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; methanesulfonyl chloride; In methanol; dichloromethane; water; acetone;

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

Reference yield:

Acetic acid (1S,2R,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester (222545-15-5) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

2: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

3: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

4: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

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

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; methanesulfonyl chloride; In methanol; dichloromethane;

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

upstream raw materials:

carbon disulfide

(1R,2S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-2-(tetrahydropyran-2-yl)oxy-cyclohex-3-en-1-ol

methyl iodide

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

Downstream raw materials:

(1R,4S,5S)-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol

(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

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