3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

Base Information

• Chemical Name: 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose
• CAS No.: 322390-89-6
• Molecular Formula: C₄₄H₄₄O₆
• Molecular Weight: 668.83

Synonyms:3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

Chemical Property of 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

There total 6 articles about 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose 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: 70.0%

benzyl bromide (100-39-0) + 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-88-5) → 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-89-6)

Guidance literature:

1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose; With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Further stages.;

DOI:10.1039/b006082h

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-89-6)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether; tetrahydrofuran

2: acetic acid

3: pyridine

4: sodium hydride / dimethylformamide

With pyridine; sodium hydride; acetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; 1: Grignard addition;

DOI:10.1081/NCN-100002543

Reference yield:

1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose (151426-71-0) → 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: sodium hydride / dimethylformamide

With pyridine; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-100002543

upstream raw materials:

benzyl bromide

1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose

Downstream raw materials:

Methyl 3,5-di-O-benzyl-3-C-vinyl-α-D-allofuranoside

Methyl 3,5-di-O-benzyl-2,6-bis(O-methylsulfonyl)-3-C-vinyl-β-D-allofuranoside

Methyl 3,5-di-O-benzyl-2,6-bis(O-methylsulfonyl)-3-C-vinyl-α-D-allofuranoside

(1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

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