2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

Base Information

• Chemical Name: 2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline
• CAS No.: 74857-71-9
• Molecular Formula: C₁₄H₁₆INO₄
• Molecular Weight: 389.19

Synonyms:2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

Chemical Property of 2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

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Technology Process of 2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

There total 7 articles about 2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 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%

methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside (74857-70-8) → 2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ2'-oxazoline (74857-71-9)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In chloroform; for 4h; Ambient temperature;

DOI:10.1139/v84-261

Reference yield: 80.0%

methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside (74857-70-8) → (3aR,6R,7R,7aR)-3a-Iodomethyl-6-methoxy-2-phenyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazol-7-ol (74857-71-9)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In chloroform;

DOI:10.1021/ja00531a050

Reference yield:

benzoyl chloride (98-88-4) → (3aR,6R,7R,7aR)-3a-Iodomethyl-6-methoxy-2-phenyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazol-7-ol (74857-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / LiAlH₄

2: 80 percent / iodonium dicollidine perchlorate / CHCl₃

With lithium aluminium tetrahydride; iodonium di(2,4,6-trimethylpyridine) perchlorate; In chloroform;

DOI:10.1021/ja00531a050

upstream raw materials:

methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

benzoyl chloride

methyl 2,3-anhydro-4-C-methylene-β-D-erythro-pentopyranoside

methyl 3-azido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

Downstream raw materials:

2'-phenyl-(methyl 3,4-dideoxy-4-C-methyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

N-((2R,3R,4R,5R)-3,5-Dihydroxy-2-methoxy-5-methyl-tetrahydro-pyran-4-yl)-benzamide

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