methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

Base Information

Chemical Name:methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate
CAS No.:1391974-06-3
Molecular Formula:C₃₇H₅₈O₇Si₂
Molecular Weight:671.034
Hs Code.:

Synonyms:methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

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Chemical Property of methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

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Technology Process of methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

There total 7 articles about methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate 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: 91.0%

: 1391973-91-3
{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 1391974-06-3
methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

: 1391973-87-7
methyl (2E)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 60 ℃; for 22h; Inert atmosphere;
DOI:10.1002/anie.201201826

Reference yield:

: 2280-44-6
D-Glucose

: 1391974-06-3
methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

: 1391973-87-7
methyl (2E)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine; p-toluenesulfonyl chloride; potassium hydroxide / 15 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / Inert atmosphere; Cooling with ice

2.2: 15 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 22 h / 0 - 20 °C / Inert atmosphere

4.1: iodine / dichloromethane / 0.92 h / 0 °C / Inert atmosphere

5.1: chloro-trimethyl-silane / tetrahydrofuran; water; ethylene dibromide / 1 h / 20 °C / Inert atmosphere

6.1: 1H-imidazole / N,N-dimethyl-formamide / 42 h / 20 °C / Inert atmosphere

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 22 h / 60 °C / Inert atmosphere

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; iodine; sodium hydride; p-toluenesulfonyl chloride; potassium hydroxide; In tetrahydrofuran; dichloromethane; water; ethylene dibromide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1002/anie.201201826

Reference yield:

: [(3aR,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-2-(iodomethyl)-hexahydro-2H-furo[3,2-b]pyran-5-yl]methanol

: 1391974-06-3
methyl (2Z)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

: 1391973-87-7
methyl (2E)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: chloro-trimethyl-silane / tetrahydrofuran; water; ethylene dibromide / 1 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 42 h / 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 22 h / 60 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chloro-trimethyl-silane; In tetrahydrofuran; water; ethylene dibromide; N,N-dimethyl-formamide; toluene;
DOI:10.1002/anie.201201826