methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

Base Information

Chemical Name:methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside
CAS No.:91312-61-7
Molecular Formula:C₃₂H₄₂O₄Si
Molecular Weight:518.769
Hs Code.:

Synonyms:methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

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Chemical Property of methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

Chemical Property:

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Technology Process of methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

There total 2 articles about methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside 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: 93.0%

: 91312-60-6
methyl 2,3-dideoxy-6-O-trityl-α-D-erythro-hexopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 91312-61-7
methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

: tert-Butyl-((2R,3S,6S)-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 8h; Title compound not separated from byproducts;
DOI:10.1021/jo00195a023

Reference yield:

: 73541-95-4
methyl 3,4-anhydro-2-deoxy-6-O-(triphenylmethyl)-α-D-ribo-hexopyranoside

: 91312-61-7
methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

2: 93 percent / imidazole / dimethylformamide / 8 h / 50 °C

With 1H-imidazole; lithium aluminium tetrahydride; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo00195a023

Reference yield:

: 91312-61-7
methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

: 476461-13-9
2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: Na / diethyl ether; liquid ammonia / 0.83 h / -78 - 22 °C

1.2: 98 percent / ammonium chloride / diethyl ether / 12 h / 22 °C

2.1: 98 percent / DMSO; (COCl)2; ET₃N / CH₂Cl₂ / 2.33 h / -78 - 22 °C

3.1: triphenylphosphine; zinc / CH₂Cl₂ / 22 °C

3.2: 63 percent / triphenylphosphine; zinc / CH₂Cl₂ / 22 °C

4.1: 88 percent / HF / acetonitrile; H₂O / 0.67 h / 0 °C

5.1: sodium hydride / tetrahydrofuran; various solvent(s) / 1.5 h / 0 °C

5.2: 94 percent / sodium iodide / tetrahydrofuran; various solvent(s) / 22.5 h / 20 °C

With oxalyl dichloride; hydrogen fluoride; sodium; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; ammonia; water; acetonitrile; 2.1: Swern oxidation;
DOI:10.1021/ol0201557