3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

Base Information

Chemical Name:3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol
CAS No.:279684-78-5
Molecular Formula:C₃₈H₄₆O₃Si₂
Molecular Weight:606.952
Hs Code.:

Synonyms:3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

Suppliers and Price of 3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

There total 10 articles about 3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-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: 80.0%

: 279684-75-2
(2S,3R,4R)-3,4-bis(tert-butyldiphenylsiloxy)-hex-5-yn-2-ol

: 279684-78-5
3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

Guidance literature:: With tungsten hexacarbonyl; triethylamine; In tetrahydrofuran; at 50 - 65 ℃; for 5h; UV-irradiation;
DOI:10.1021/ja994229u

Reference yield:

: 53723-96-9
(2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one

: 279684-78-5
3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

Guidance literature:: Multi-step reaction with 10 steps

1: 91 percent / BH₃-SMe₂; (R)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 3.5 h / -45 °C

2: 76 percent / cumene hydroperoxide; Ti(O-i-Pr)4; L-(+)-diisopropyl tartrate / CH₂Cl₂ / 5.5 h / -30 °C

3: 94 percent / Ph₃P; DEAD / diethyl ether / 4 h / 20 °C

4: 92 percent / KCN; MeOH / 11 h

5: 91 percent / Ti(O-i-Pr)4 / benzene / 70 °C

6: 100 percent / imidazole / dimethylformamide / 24 h / 20 °C

7: 95 percent / DIBAL / CH₂Cl₂ / -70 °C

8: 55 percent / Ph₃P; DEAD / diethyl ether / 72 h

9: 93 percent / DIBAL / CH₂Cl₂ / -70 °C

10: 80 percent / W(CO)6; Et₃N / tetrahydrofuran / 5 h / 50 - 65 °C / UV-irradiation

With 1H-imidazole; titanium(IV) isopropylate; methanol; potassium cyanide; tungsten hexacarbonyl; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; dimethylsulfide borane complex; diisobutylaluminium hydride; triethylamine; triphenylphosphine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Mitsunobu reaction / 4: debenzoylation / 5: Addition / 6: silylation / 7: deacylation / 8: Mitsunobu reaction / 9: deacylation / 10: Cyclization;
DOI:10.1021/ja994229u

Reference yield:

: 279684-67-2
(3R,4R,5S)-4,5-epoxyhex-1-yn-3-ol

: 279684-78-5
3,4-bis-(tert-butyldiphenylsilyl)-1,5-anhydro-2,6-dideoxy-L-xylo-hex-1-enitol

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / Ti(O-i-Pr)4 / benzene / 70 °C

2: 100 percent / imidazole / dimethylformamide / 24 h / 20 °C

3: 95 percent / DIBAL / CH₂Cl₂ / -70 °C

4: 55 percent / Ph₃P; DEAD / diethyl ether / 72 h

5: 93 percent / DIBAL / CH₂Cl₂ / -70 °C

6: 80 percent / W(CO)6; Et₃N / tetrahydrofuran / 5 h / 50 - 65 °C / UV-irradiation

With 1H-imidazole; titanium(IV) isopropylate; tungsten hexacarbonyl; diisobutylaluminium hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Addition / 2: silylation / 3: deacylation / 4: Mitsunobu reaction / 5: deacylation / 6: Cyclization;
DOI:10.1021/ja994229u