3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

Base Information

Chemical Name:3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one
CAS No.:138607-78-0
Molecular Formula:C₂₃H₂₄O₆
Molecular Weight:396.44
Hs Code.:

Synonyms:3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

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Chemical Property of 3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

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Technology Process of 3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

There total 4 articles about 3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one 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: 85.0%

: [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-dihydro-pyran-(3Z)-ylidene]-acetic acid methyl ester

: 138607-78-0
3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 3h;
DOI:10.1021/jo00028a017

Reference yield: 71.0%

: 740840-46-4
(Diethoxy-phosphoryl)-acetic acid (2R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-oxo-tetrahydro-pyran-2-ylmethyl ester

: 138607-78-0
3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 20 ℃; for 24h;
DOI:10.1002/anie.200353478

Reference yield:

: 17791-36-5
methyl 2,3-di-O-benzyl-α-D-glucopyranoside

: 138607-78-0
3,4-dibenzyloxy-2-methoxy-3,4,8,8a-tetrahydro-2H-pyrano[3,4-b]pyran-6-one

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / DCC; 4-DMAP / CH₂Cl₂ / 4 h / 20 °C

2: 75 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 71 percent / N,N-diisopropylethylamine; LiCl / acetonitrile / 24 h / 20 °C

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium chloride; In dichloromethane; acetonitrile; 2: Swern oxidation / 3: Nasamune-Roush olefination;
DOI:10.1002/anie.200353478