(3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

Chemical Name:(3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol
CAS No.:202339-19-3
Molecular Formula:C₂₃H₂₈O₆
Molecular Weight:400.472
Hs Code.:

Synonyms:(3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Property of (3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Technology Process of (3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

There total 5 articles about (3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]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: 55.0%

: 202339-17-1
(2S,3R,4S,4aR,7R,8aR)-3,4-Bis-benzyloxy-2-methoxy-7-methoxymethoxy-octahydro-pyrano[3,2-b]pyran

: 202339-19-3
(3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: With hydrogenchloride; In water; acetic acid; at 120 ℃; for 1h;
DOI:10.1271/bbb.61.2019

Reference yield:

: Toluene-4-sulfonic acid (R)-3-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-propyl ester

: 202339-19-3
(3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / DIPEA / CH₂Cl₂

2: 80 percent / DDQ / CH₂Cl₂ / 2 h / Ambient temperature

3: 87 percent / 15-crown-5, NaH / dimethylformamide / 0.17 h / Ambient temperature

4: 55 percent / HCl / acetic acid; H₂O / 1 h / 120 °C

With hydrogenchloride; 15-crown-5; sodium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1271/bbb.61.2019

Reference yield:

: Toluene-4-sulfonic acid (R)-3-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-2-methoxymethoxy-propyl ester

: 202339-19-3
(3R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / DDQ / CH₂Cl₂ / 2 h / Ambient temperature

2: 87 percent / 15-crown-5, NaH / dimethylformamide / 0.17 h / Ambient temperature

3: 55 percent / HCl / acetic acid; H₂O / 1 h / 120 °C

With hydrogenchloride; 15-crown-5; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1271/bbb.61.2019