4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol

Base Information

• Chemical Name: 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol
• CAS No.: 931430-96-5
• Molecular Formula: C₂₁H₃₆O₄Si
• Molecular Weight: 380.6

Synonyms:4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol

Chemical Property of 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol

Chemical Property:

Purity/Quality:

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Technology Process of 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol

There total 3 articles about 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol 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: 94.0%

4-O-benzyl-2,3-O-isopropylidene-2-C-methyl-D-erythritol (931430-92-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol (931430-96-5)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1016/j.tet.2006.12.078

Reference yield:

2,3-O-isopropylidene-2-C-(p-toluenesulfonyloxymethyl)-D-erythrofuranose (931430-90-9) → 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol (931430-96-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / LiAlH₄ / tetrahydrofuran / 10 h / Heating

2.1: NaH / tetrahydrofuran / 25 °C

2.2: tetrahydrofuran / 25 °C

3.1: 94 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2006.12.078

Reference yield:

2-C-methyl-2,3-O-isopropylidene-D-erythritol (77587-29-2) → 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol (931430-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 25 °C

1.2: tetrahydrofuran / 25 °C

2.1: 94 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2006.12.078

upstream raw materials:

4-O-benzyl-2,3-O-isopropylidene-2-C-methyl-D-erythritol

tert-butyldimethylsilyl chloride

2,3-O-isopropylidene-2-C-(p-toluenesulfonyloxymethyl)-D-erythrofuranose

2-C-methyl-2,3-O-isopropylidene-D-erythritol

Downstream raw materials:

Phosphoric acid dibenzyl ester (4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl ester

2-C-methyl-D-erythritol 4-phosphate

2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate

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