methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside
• CAS No.: 141438-55-3
• Molecular Formula: C₂₂H₂₆INO₆
• Molecular Weight: 527.356

Synonyms:methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Chemical Property of methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

There total 5 articles about methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 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: 75.0%

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5) → methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside (141438-55-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 80 ℃;

DOI:10.1016/S0040-4039(00)60336-2

Reference yield:

benzyl bromide (100-39-0) → methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside (141438-55-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.5 h / 0 °C

2: 92 percent / CH₃COCl, CH₃OH / 2 h / 24 °C

3: 75 percent / I₂, PPh₃, pyridine / toluene / 4 h / 70 °C

With pyridine; methanol; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; acetyl chloride; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1021/jo00039a044

Reference yield:

methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-53-1) → methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside (141438-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / CH₃COCl, CH₃OH / 2 h / 24 °C

2: 75 percent / I₂, PPh₃, pyridine / toluene / 4 h / 70 °C

With pyridine; methanol; iodine; acetyl chloride; triphenylphosphine; In toluene;

DOI:10.1021/jo00039a044

upstream raw materials:

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl bromide

methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Downstream raw materials:

methyl 4-O-acetyl-2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-(4-methoxy-benzyl)-carbamic acid benzyl ester

(3aS,4R,5R,6S,7aS)-4,6-Bis-benzyloxy-5-hydroxy-hexahydro-benzooxazol-2-one

(3aS,4R,5R,6S,7aS)-4,6-Bis-benzyloxy-2-dimethylamino-3a,4,5,6,7,7a-hexahydro-benzooxazol-5-ol

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