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

Base Information

• Chemical Name: (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butan-1-ol
• CAS No.: 210765-02-9
• Molecular Formula: C₃₂H₅₀O₆Si
• Molecular Weight: 558.831

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

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

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>butan-1-ol

There total 19 articles about (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butan-1-ol 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:

(3S,3aS,4S,5S,7S,7aS)-7-iodo-4,5-di-(4-methoxybenzyl)oxy-3-methyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (210764-99-1) → (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)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

2: DIBAL / toluene / 0.17 h / -78 °C

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

4: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; borane-THF; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; In dichloromethane; toluene; benzene;

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

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>butan-1-ol (210765-02-9)

Guidance literature:

Multi-step reaction with 3 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

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; borane-THF; dihydrogen peroxide; In 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) → (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)

Guidance literature:

Multi-step reaction with 16 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

8: 96 percent / PPTS / ethanol / 3 h / 50 °C

9: 74 percent / propionic acid / 2 h / 140 °C

10: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

11: 87 percent / aq. NaHCO₃, KI, I₂ / tetrahydrofuran / 2 h / Ambient temperature

12: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

13: DIBAL / toluene / 0.17 h / -78 °C

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

15: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

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

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

upstream raw materials:

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

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:

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

(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

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