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

Base Information

• Chemical Name: (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol
• CAS No.: 222545-21-3
• Molecular Formula: C₃₂H₄₈O₆Si
• Molecular Weight: 556.815

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 23 articles about (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-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: 93.0%

(2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-enal (210765-04-1) → (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol (222545-21-3)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.25h;

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

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) → (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol (222545-21-3)

Guidance literature:

Multi-step reaction with 9 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

6: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

7: KN(SiMe₃)2, Et₃N / tetrahydrofuran / 0.33 h / 0 °C

8: Pd)OAc)2 / acetonitrile / 12 h / 0 °C

9: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

With 2,6-dimethylpyridine; palladium diacetate; sodium hydroxide; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;

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

Reference yield:

(1R,2R,3S,4S)-3-<(1R)-1-methylprop-2-en-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane (222545-20-2) → (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol (222545-21-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

3: KN(SiMe₃)2, Et₃N / tetrahydrofuran / 0.33 h / 0 °C

4: Pd)OAc)2 / acetonitrile / 12 h / 0 °C

5: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

With palladium diacetate; sodium hydroxide; tetrapropylammonium perruthennate; borane-THF; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

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

upstream raw materials:

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

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:

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

(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

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

(2E)-3-<(3R,4S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-1-oxaspiro<2.5>oct-4-yl>-1-(tert-butyldimethylsilyl)oxybut-2-ene

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