(3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol

Base Information

• Chemical Name: (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol
• CAS No.: 118299-07-3
• Molecular Formula: C₂₂H₃₄O₆
• Molecular Weight: 394.508

Synonyms:(3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol

Chemical Property of (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol

There total 15 articles about (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol 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:

(E)-(5S,6R,7S)-6-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,7-dimethoxy-3-methyl-hept-3-enal (126502-52-1) → (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol (118299-07-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;

DOI:10.1021/jo00296a041

Reference yield:

(3S,4R,5S)-4-Benzyloxy-3,5-dimethoxy-hexane-1,2,6-triol (126502-45-2) → (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol (118299-07-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / TsOH, 3-A molecular sieves / Ambient temperature

2: (ClCO)2, DMSO, TEA / CH₂Cl₂ / -78 °C

3: CH₂Cl₂ / from 0 deg C to RT

4: 100 percent / LiEt₃BH / tetrahydrofuran / -78 - -20 °C

5: 67 percent / MsCl, LiCl, s-collidine / dimethylformamide / 0 °C

6: 69 percent / dimethylformamide / Ambient temperature

7: 1.) (i-Bu₂)AlH, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) ethanol, RT

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; TEA; diisobutylaluminium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00262a006

Reference yield:

(2S,3R,4S)-3-Benzyloxy-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethoxy-butan-1-ol (126502-46-3) → (3E)-2,3,4-Trideoxy-3-methyl-5,7-di-O-methyl-8,9-O-(1-methylethylidene)-6-O-(phenylmethyl)-D-galacto-non-3-enitol (118299-07-3)

Guidance literature:

Multi-step reaction with 6 steps

1: (ClCO)2, DMSO, TEA / CH₂Cl₂ / -78 °C

2: CH₂Cl₂ / from 0 deg C to RT

3: 100 percent / LiEt₃BH / tetrahydrofuran / -78 - -20 °C

4: 67 percent / MsCl, LiCl, s-collidine / dimethylformamide / 0 °C

5: 69 percent / dimethylformamide / Ambient temperature

6: 1.) (i-Bu₂)AlH, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) ethanol, RT

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; oxalyl dichloride; TEA; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00262a006

upstream raw materials:

(E)-(5S,6R,7S)-6-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,7-dimethoxy-3-methyl-hept-3-enal

(E)-(5S,6R,7S)-6-Benzyloxy-7-(2,2-dimethyl-[1,3]dioxolan-4-yl)-5,7-dimethoxy-3-methyl-hept-3-enenitrile

(3S,4R,5S)-4-Benzyloxy-3,5-dimethoxy-hexane-1,2,6-triol

(2S,3R,4S)-3-Benzyloxy-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethoxy-butan-1-ol

Downstream raw materials:

Benzoic acid (3E,8E)-(5S,6R,7S)-6-hydroxy-5,7-dimethoxy-9-methoxycarbonyl-3-methyl-deca-3,8-dienyl ester

[(1R,2S,4R)-6-Benzenesulfonyl-1-((1S,3R)-3-[1,3]dithian-2-yl-1-methoxy-butyl)-2-methoxy-4-methyl-heptyloxy]-tert-butyl-dimethyl-silane

<1R-<1R*,(1S*,3R*),2S*,4R*>>-(1,1-Dimethylethyl)<<1-<3-(1,3-dithian-2-yl)-1-methoxybutyl>-2-methoxy-4-methyl-6-(phenylsulfonyl)hexyl>oxy>dimethylsilane

<γS-(γR*,εR*,ξS*,ηR*,ιS*)>-ξ-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-ε,η-dimethoxy-γ,ι-dimethyl-1,3-dithiane-2-nonanol-benzoate

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