(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol
CAS No.:904300-34-1
Molecular Formula:C₅₈H₆₈O₉SSi
Molecular Weight:969.324
Hs Code.:

(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Synonyms:(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

There total 3 articles about (2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol 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: 54.0%

: 904300-32-9
ethyl 4-deoxy-6-O-tert-butyldiphenylsilyl-1-thio-α-D-lyxo-hexopyranoside

: 67773-43-7
2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide

: 904300-34-1
(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Guidance literature:: With 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 36h;
DOI:10.1016/j.carres.2006.03.015

Reference yield:

: tert-Butyl-((3aS,4R,6S,7aS)-4-ethylsulfanyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-diphenyl-silane

: 904300-34-1
(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 140 mg / aq. TFA / acetic acid / 2 h / 0 °C

2: 54 percent / Et₄NBr; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide / 36 h / 20 °C

With 4 A molecular sieve; tetraethylammonium bromide; trifluoroacetic acid; In dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2006.03.015

Reference yield:

: 316188-13-3
ethyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

: 904300-34-1
(2R,3S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,1'-thiocarbonyldiimidazole / CH₂Cl₂ / 10 h / Heating

1.2: Bu₃SnH; AIBN / benzene / 0.17 h / Heating

2.1: 140 mg / aq. TFA / acetic acid / 2 h / 0 °C

3.1: 54 percent / Et₄NBr; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide / 36 h / 20 °C

With 4 A molecular sieve; tetraethylammonium bromide; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; In dichloromethane; acetic acid; N,N-dimethyl-formamide; 1.2: Barton-McCombie deoxygenation;
DOI:10.1016/j.carres.2006.03.015