(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

Base Information

Chemical Name:(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde
CAS No.:402474-66-2
Molecular Formula:C₂₅H₃₄O₅Si
Molecular Weight:442.627
Hs Code.:

Synonyms:(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

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Chemical Property of (S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

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Technology Process of (S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

There total 8 articles about (S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-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: 86.0%

: 405116-14-5
(R)-2-Benzyloxy-2-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-ethanol

: 402474-66-2
(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1h;
DOI:10.1016/S0040-4020(01)01074-2

Reference yield:

: 18685-18-2,22331-21-1,23885-38-3,40982-92-1,65451-98-1,101475-83-6,134275-38-0,145625-96-3
3-O-benzyl-1,2:5,6-di-O-isopropylidene-D-glucofuranose

: 402474-66-2
(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 74 percent / 1N H₂SO₄ / dioxane / 70 °C

2: 85 percent / CSA / dimethylformamide / 8 h / 25 °C

3: 98 percent / Pb(OAc)4 / ethyl acetate / 0.5 h / 0 °C

4: 56 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5: 76 percent / pyridine / 3 h / 0 - 20 °C

6: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 4.5 g / MeONa / methanol / 0.5 h / 0 °C

8: 86 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; sodium methylate; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01074-2

Reference yield:

: 65877-63-6,97590-76-6,99396-09-5,5531-09-9
3-O-benzyl-D-glucopyranose

: 402474-66-2
(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / CSA / dimethylformamide / 8 h / 25 °C

2: 98 percent / Pb(OAc)4 / ethyl acetate / 0.5 h / 0 °C

3: 56 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4: 76 percent / pyridine / 3 h / 0 - 20 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 4.5 g / MeONa / methanol / 0.5 h / 0 °C

7: 86 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; sodium methylate; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01074-2