3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol

Base Information

• Chemical Name: 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol
• CAS No.: 106799-18-2
• Molecular Formula: C₂₂H₃₈O₄Si
• Molecular Weight: 394.627
• Mol file: 106799-18-2.mol

Synonyms:3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol

Chemical Property of 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol

There total 23 articles about 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol 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: 93.0%

(2R,4R)-1-Benzyloxy-6-(1-methyl-1-trimethylsilanyl-ethoxy)-hexane-2,4-diol + 2,2-dimethoxy-propane (77-76-9) → 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol (106799-18-2)

Guidance literature:

camphor-10-sulfonic acid; at 25 ℃; for 1h;

DOI:10.1021/ja00241a062

Reference yield:

(2R,4S)-1-<(phenylmethoxy)methyl>5-hexene-2,4-diol (106799-17-1) → 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol (106799-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / CSA / 1 h / 25 °C

2: 93 percent / 2-methyl-2-butene, BH₃*THF / tetrahydrofuran / 1.5 h / 0 °C

3: 92 percent / imidazole / dimethylformamide / 1 h / 0 - 25 °C

With 1H-imidazole; borane-THF; 2-methyl-but-2-ene; camphor-10-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a028

Reference yield:

(E)-4-(benzyloxy)-2-buten-1-ol (80885-30-9,81028-03-7,69152-88-1) → 3,5-dideoxy-6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol (106799-18-2)

Guidance literature:

Multi-step reaction with 11 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: benzene / 16 h / Ambient temperature

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

5: pyridine / 3 h / 0 °C

6: imidazole / dimethylformamide / 1.5 h / Ambient temperature

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

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

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

10: 90 percent / imidazole / dimethylformamide / 2 h / 25 °C

11: 95 percent / CSA / 0.5 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; camphor-10-sulfonic acid; In tetrahydrofuran; pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00222a028

upstream raw materials:

2,2-dimethoxy-propane

(E)-4-(benzyloxy)-2-buten-1-ol

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol

(2R,3S)-3-Benzyloxymethyl-oxirane-2-carbaldehyde