(+/-)-(3R,4R,1'S*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone

Base Information

Chemical Name:(+/-)-(3R*,4R*,1'S*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone
CAS No.:142677-28-9
Molecular Formula:C₂₁H₃₄O₇Si
Molecular Weight:426.582
Hs Code.:

Synonyms:

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Chemical Property of (+/-)-(3R*,4R*,1'S*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone

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Technology Process of (+/-)-(3R*,4R*,1'S*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone

There total 14 articles about (+/-)-(3R*,4R*,1'S*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone 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:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 142677-28-9,142759-14-6
(+/-)-(3R*,4R*,1'R*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / p-TsOH / CH₂Cl₂ / 12 h / Heating

2: 83 percent / NaOH, PhCH₂(n-Bu)3NBr / CH₂Cl₂; H₂O / 16 h / Ambient temperature

3: 34 percent / LDA / tetrahydrofuran / 3 h / -75 °C

4: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 40 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

6: OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

7: 1.) NaIO₄, 2.) Ag₂CO₃ celite / 1.) aq. EtOAc, 2.) benzene, 30 min, reflux

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; benzyl tri-n-butylammonium bromide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 142677-28-9,142759-14-6
(+/-)-(3R*,4R*,1'S*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / p-TsOH / CH₂Cl₂ / 12 h / Heating

2: 83 percent / NaOH, PhCH₂(n-Bu)3NBr / CH₂Cl₂; H₂O / 16 h / Ambient temperature

3: 40 percent / LDA / tetrahydrofuran / 3 h / -75 °C

4: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

6: OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

7: 1.) NaIO₄, 2.) Ag₂CO₃ celite / 1.) aq. EtOAc, 2.) benzene, 30 min, reflux

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; benzyl tri-n-butylammonium bromide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

Reference yield:

: 131223-63-7
2-hydroxy-5-(methoxymethoxy)benzaldehyde

: 142677-28-9,142759-14-6
(+/-)-(3R*,4R*,1'R*)-4-<1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-5-methoxymethoxyphenyl)methyl>-3-hydroxymethyl-2(3H)-furanone

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / NaOH, PhCH₂(n-Bu)3NBr / CH₂Cl₂; H₂O / 16 h / Ambient temperature

2: 34 percent / LDA / tetrahydrofuran / 3 h / -75 °C

3: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 40 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

5: OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

6: 1.) NaIO₄, 2.) Ag₂CO₃ celite / 1.) aq. EtOAc, 2.) benzene, 30 min, reflux

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; benzyl tri-n-butylammonium bromide; 4-methylmorpholine N-oxide; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;