3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Base Information

• Chemical Name: 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose
• CAS No.: 457067-99-1
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.412

Synonyms:3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Chemical Property of 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Chemical Property:

Purity/Quality:

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Technology Process of 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

There total 10 articles about 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 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: 82.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (457067-99-1)

Guidance literature:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose; With periodic acid; In ethyl acetate;

formaldehyd; With sodium hydroxide; In tetrahydrofuran;

With sodium tetrahydroborate; Further stages.;

DOI:10.1039/b205031e

Reference yield: 65.0%

formic acid (64-18-6) + 3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (457067-99-1)

Guidance literature:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose; With acetic acid; In water; at 60 ℃;

With sodium periodate; In tetrahydrofuran; water; at 0 ℃;

formic acid; With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/S0040-4039(02)00784-0

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (3aR,5S,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (136152-95-9) → 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (457067-99-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 18h;

DOI:10.1021/jo051187l

upstream raw materials:

formaldehyd

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

formic acid

(R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

Downstream raw materials:

3-C-allyl-3,5-di-O-benzyl-4-C-hydroxymethyl-1,2-di-O-isopropylidene-α-D-ribofuranose

3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-hydroxyallyl)-1,2-di-O-isopropylidene-α-D-ribofuranose

3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-1,2-di-O-isopropylidene-α-D-ribofuranose

(1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-ene

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