methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside

Base Information

• Chemical Name: methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside
• CAS No.: 1207164-11-1
• Molecular Formula: C₂₉H₃₁BrO₅
• Molecular Weight: 539.466

Synonyms:methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside

Chemical Property of methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside

Chemical Property:

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Technology Process of methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside

There total 4 articles about methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside 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: 49.0%

sodium methylate (124-41-4) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-gulo-hexitol → methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside (1207164-11-1) + methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-α-D-arabino-hexopyranoside (1207164-10-0)

Guidance literature:

In tetrahydrofuran; for 1.25h; Reflux;

DOI:10.1021/jo902306a

Reference yield: 36.0%

methanol (67-56-1) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-talohexitol → methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside (1207164-11-1) + methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-α-D-arabino-hexopyranoside (1207164-10-0)

Guidance literature:

methanol; With sodium; Inert atmosphere;

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-talohexitol; In tetrahydrofuran; for 3h; Overall yield = 48 percent; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.1c02366

Reference yield:

methanol (67-56-1) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-gulo-hexitol → methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-β-D-arabino-hexopyranoside (1207164-11-1) + methyl (2E)-3,4,6-tri-O-benzyl-2-C-(bromomethylene)-2-deoxy-α-D-arabino-hexopyranoside (1207164-10-0)

Guidance literature:

methanol; With sodium; In tetrahydrofuran; at 20 ℃; for 0.005h; Inert atmosphere;

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-gulo-hexitol; In tetrahydrofuran; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1021/acs.joc.1c02366

upstream raw materials:

sodium methylate

methanol

deuteromethanol

Downstream raw materials:

(2E)-methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-3,4,6-tri-O-benzyl-2-methylene-β-D-glucopyranoside

(2E)-methyl-(3,4,6-tri-O-benzyl-1-deoxy-α-D-glucopyranosyl)-(1?7C)-3,4,6-tri-O-benzyl-2-methylene-β-D-glucopyranoside

(2E)-methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-3,4,6-tri-O-benzyl-2-methylene-β-D-glucopyranoside

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