methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

Base Information

Chemical Name:methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate
CAS No.:343981-95-3
Molecular Formula:C₂₈H₅₀O₆Si₂
Molecular Weight:538.872
Hs Code.:

Synonyms:methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

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Chemical Property of methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

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Technology Process of methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

There total 8 articles about methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate 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: 95.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 343981-94-2
methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-6-hydroxy-7-(4-methoxybenzyl)oxy-2-heptenoate

: 343981-95-3
methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

Guidance literature:: With triethylamine; In dichloromethane; at -30 ℃; for 0.5h;
DOI:10.1021/ja010195q

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 343981-95-3
methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

With dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; acetonitrile; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; 4: Sharpless assymetric dihydroxylation;
DOI:10.1021/ja010195q

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 343981-95-3
methyl (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenoate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

With dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; acetonitrile; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; 4: Sharpless assymetric dihydroxylation;
DOI:10.1021/ja010195q