(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol
• CAS No.: 748154-79-2
• Molecular Formula: C₁₅H₂₁IO₅
• Molecular Weight: 408.233
• Mol file: 748154-79-2.mol

Synonyms:(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Chemical Property of (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

There total 8 articles about (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol 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: 100.0%

methyl 3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside (226885-88-7) → (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside (226885-87-6) → (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / AcOH; H₂O / 70 °C

2: 100 percent / I₂; Ph₃P; Imid_. / toluene

With 1H-imidazole; water; iodine; acetic acid; triphenylphosphine; In toluene;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside (72904-78-0) → (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NaH / dimethylformamide / 20 °C

2: 80 percent / AcOH; H₂O / 70 °C

3: 100 percent / I₂; Ph₃P; Imid_. / toluene

With 1H-imidazole; water; iodine; sodium hydride; acetic acid; triphenylphosphine; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2004.05.129

upstream raw materials:

methyl 3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside

D-glucose

methyl-alpha-D-glucopyranoside

methyl 4,6-O-benzylidene-3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside

Downstream raw materials:

methyl 3,6-dideoxy-6-iodo-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-arabinopyranoside

6-hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-cyclohexanone