2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

Base Information

Chemical Name:2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)
CAS No.:114861-31-3
Molecular Formula:C₁₈H₂₈O₅
Molecular Weight:324.417
Hs Code.:

Synonyms:2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

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Chemical Property of 2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

Chemical Property:

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Technology Process of 2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

There total 10 articles about 2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate) 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: 88.0%

: 3282-30-2
pivaloyl chloride

: 81120-67-4
2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol

: 114861-31-3
2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

Guidance literature:: With pyridine; at 0 ℃; for 6h;
DOI:10.1021/ja00241a062

Reference yield:

: 80885-30-9,81028-03-7,69152-88-1
(E)-4-(benzyloxy)-2-buten-1-ol

: 114861-31-3
2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) D-(-)-diethyltartarate, Ti(O-i-Pr)4, t-BuOOH; 2.) Me₂S, 10percent aq. tartaric acid / 1.) CH₂Cl₂, - 23 deg C, 5 h; 2.) CH₂Cl₂, -23 to 25 deg C, 1.5 h

2: 1.) oxallyl chloride, DMSO; 3.) triethylamine

3: 77 percent / benzene / 16 h / Ambient temperature

4: 82 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

5: 95 percent / pyridine / 3 h / 0 °C

6: 96 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

7: 87 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

8: Ti(O-i-Pr)4, D-(-)-diethyltartarate, t-BuOOH / CH₂Cl₂ / 16 h / -20 °C

9: 85 percent / Red-Al / tetrahydrofuran / 3 h / Ambient temperature

10: 88 percent / 4-(dimethylamino)pyridine / pyridine / 5 h / Ambient temperature

With oxallyl chloride; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; tartaric acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; dmap; In tetrahydrofuran; pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00222a028

Reference yield:

: 78513-15-2
<2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranemethanol

: 114861-31-3
2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol 1-(2,2-dimethyl-propanoate)

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) oxallyl chloride, DMSO; 3.) triethylamine

2: 77 percent / benzene / 16 h / Ambient temperature

3: 82 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

4: 95 percent / pyridine / 3 h / 0 °C

5: 96 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

6: 87 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

7: Ti(O-i-Pr)4, D-(-)-diethyltartarate, t-BuOOH / CH₂Cl₂ / 16 h / -20 °C

8: 85 percent / Red-Al / tetrahydrofuran / 3 h / Ambient temperature

9: 88 percent / 4-(dimethylamino)pyridine / pyridine / 5 h / Ambient temperature

With oxallyl chloride; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; dmap; In tetrahydrofuran; pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00222a028