(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran
CAS No.:239803-09-9
Molecular Formula:C₅₇H₆₈O₆Si₂
Molecular Weight:905.334
Hs Code.:

(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

Synonyms:(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

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Technology Process of (2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

There total 6 articles about (2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran 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: 92.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 239803-08-8
(2S,3S,4R,5S,6R)-2-Allyloxy-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran-4-ol

: 239803-09-9
(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

Guidance literature:: With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 110 ℃;
DOI:10.1016/S0040-4039(99)01077-1

Reference yield:

: 93381-66-9
allyl-6-O-trityl-α-D-mannopyranoside

: 239803-09-9
(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / TsOH / dimethylformamide / 2 h / 45 °C / 10 Torr

2: 62 percent / imidazole; 4-DMAP / dimethylformamide / 8 h / 100 °C

3: 69 percent / DIBALH / CH₂Cl₂ / 2 h / 0 °C

4: 89 percent / NaH / dimethylformamide / 2 h / 0 °C

5: 88 percent / DDQ / CH₂Cl₂ / 2 h / 20 °C

6: 92 percent / 2,6-lutidine / dimethylformamide / 110 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Etherification / 3: Hydrogenation / 4: Alkylation / 5: Oxidation / 6: Etherification;
DOI:10.1016/S0040-4039(99)01077-1

Reference yield:

: (3aS,4S,6R,7R,7aS)-4-Allyloxy-2-(4-methoxy-phenyl)-6-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

: 239803-09-9
(2S,3S,4R,5R,6R)-2-Allyloxy-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-6-trityloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / imidazole; 4-DMAP / dimethylformamide / 8 h / 100 °C

2: 69 percent / DIBALH / CH₂Cl₂ / 2 h / 0 °C

3: 89 percent / NaH / dimethylformamide / 2 h / 0 °C

4: 88 percent / DDQ / CH₂Cl₂ / 2 h / 20 °C

5: 92 percent / 2,6-lutidine / dimethylformamide / 110 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Hydrogenation / 3: Alkylation / 4: Oxidation / 5: Etherification;
DOI:10.1016/S0040-4039(99)01077-1