(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

Base Information

Chemical Name:(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde
CAS No.:186664-11-9
Molecular Formula:C₂₆H₃₂O₆Si
Molecular Weight:468.622
Hs Code.:

Synonyms:(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

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Chemical Property of (R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

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Technology Process of (R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

There total 6 articles about (R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde 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:

: 186664-06-2
2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide

: 186664-11-9
(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / I₂ / tetrahydrofuran; H₂O / 5 h / Heating

2: 88 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

3: 98 percent / H₃PO₂ aq., AIBN, Et₃N / dioxane / 1 h / Heating

4: 96 percent / CAN, pyridine / H₂O; acetonitrile / 0.5 h / 0 °C

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

With pyridine; 1H-imidazole; oxalyl dichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); iodine; hypophosphorous acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)82953-X

Reference yield:

: 2-[(1S,2S,5S,7S)-7-(4-Methoxy-phenoxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-yl]-N,N-dimethyl-acetamide

: 186664-11-9
(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / p-TsOH*H₂O / 7.5 h / 0 °C

2: 90 percent / I₂ / tetrahydrofuran; H₂O / 5 h / Heating

3: 88 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

4: 98 percent / H₃PO₂ aq., AIBN, Et₃N / dioxane / 1 h / Heating

5: 96 percent / CAN, pyridine / H₂O; acetonitrile / 0.5 h / 0 °C

6: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

With pyridine; 1H-imidazole; oxalyl dichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); iodine; hypophosphorous acid; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)82953-X

Reference yield:

: 186664-07-3
(3aR,4S,6S,7S,7aR)-4-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-7-iodo-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one

: 186664-11-9
(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

2: 98 percent / H₃PO₂ aq., AIBN, Et₃N / dioxane / 1 h / Heating

3: 96 percent / CAN, pyridine / H₂O; acetonitrile / 0.5 h / 0 °C

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

With pyridine; 1H-imidazole; oxalyl dichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); hypophosphorous acid; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)82953-X