(2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol
• CAS No.: 134407-67-3
• Molecular Formula: C₁₅H₂₂O₆
• Molecular Weight: 298.336

Synonyms:(2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol

Chemical Property of (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol

Chemical Property:

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Technology Process of (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol

There total 4 articles about (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol 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: 65.0%

(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methoxymethyl-tetrahydro-pyran → (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol (134407-67-3)

Guidance literature:

With acetic acid; at 70 ℃; for 18h;

DOI:10.1016/0008-6215(91)84145-5

Reference yield:

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) → (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol (134407-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / NaH / dimethylformamide / 2 h / 110 °C

2: 62 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h / Heating

3: 90 percent / methylation

4: 65 percent / 50percent HOAc / 18 h / 70 °C

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; acetic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)84145-5

Reference yield:

(4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (134407-59-3) → (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol (134407-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h / Heating

2: 90 percent / methylation

3: 65 percent / 50percent HOAc / 18 h / 70 °C

With lithium aluminium tetrahydride; aluminium trichloride; acetic acid; In diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(91)84145-5

upstream raw materials:

methyl 4,6-O-benzylidene-α-D-glucopyranoside

methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside

(4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Downstream raw materials:

4-O-acetyl-1,5-anhydro-2,3-di-O-(methoxycarbonylmethyl)-6-O-methyl-D-glucitol

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