(3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal

Base Information

• Chemical Name: (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal
• CAS No.: 210765-03-0
• Molecular Formula: C₃₂H₄₈O₆Si
• Molecular Weight: 556.815
• Mol file: 210765-03-0.mol

Synonyms:(3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal

Chemical Property of (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal

There total 20 articles about (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal 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: 81.0%

(3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butan-1-ol (210765-02-9) → (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal (210765-03-0)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane;

DOI:10.1039/a802169d

Reference yield:

(3S,3aR,4S,5S,7aR)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-octahydro-benzofuran-2-ol (222545-34-8) → (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal (210765-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 60 deg C, 3 h

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 0 deg C, 1 h

4: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; dihydrogen peroxide; 4-methylmorpholine N-oxide; In dichloromethane;

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) → (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal (210765-03-0)

Guidance literature:

Multi-step reaction with 15 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

6: 96 percent / PPTS / ethanol / 3 h / 50 °C

7: 74 percent / propionic acid / 2 h / 140 °C

8: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

9: 87 percent / aq. NaHCO₃, KI, I₂ / tetrahydrofuran / 2 h / Ambient temperature

10: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

11: DIBAL / toluene / 0.17 h / -78 °C

12: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 60 deg C, 3 h

13: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

14: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 0 deg C, 1 h

15: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; borane-THF; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; propionic acid; 4-methylmorpholine N-oxide; potassium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;

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

upstream raw materials:

(3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butan-1-ol

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-<(1E)-3-hydroxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

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

(2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol

(2S,3S,4S)-2-<(1E)-3-(tert-butyldimethylsilyl)oxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-one