(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran
• CAS No.: 354113-95-4
• Molecular Formula: C₄₁H₄₄O₈
• Molecular Weight: 664.796

Synonyms:(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran

Chemical Property of (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran

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Technology Process of (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran

There total 2 articles about (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran 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: 40.0%

methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside (134407-60-6) + 2-bromomethylnaphthyl bromide (939-26-4) → (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran (354113-95-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)00563-9

Reference yield:

methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside (199918-03-1) → (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran (354113-95-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / DIBAL-H / toluene; CH₂Cl₂

2: 40 percent / NaH / dimethylformamide

With sodium hydride; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(01)00563-9

Reference yield: 61.0%

(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran (354113-95-4) → (2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-3,4-diol

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetone;

DOI:10.1016/S0040-4039(01)00563-9

upstream raw materials:

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

2-bromomethylnaphthyl bromide

methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside

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