(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester
CAS No.:685142-66-9
Molecular Formula:C₁₆H₂₂O₇
Molecular Weight:326.346
Hs Code.:

Synonyms:(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

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Chemical Property of (2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

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Technology Process of (2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

There total 6 articles about (2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester 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: 59.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 685142-64-7
(-)-(2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-5-methoxytetrahydrofuran-2-carboxylate

: 685142-66-9
(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

: 685142-67-0
(2R,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - -10 ℃;
DOI:10.1016/j.tet.2003.07.012

Reference yield:

: 35781-73-8
(-)-(3aR,5R,6aR)-methyl 3a,5,6,6a-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carboxylate

: 685142-66-9
(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: HCl / 1 h / Heating

1.2: 3.88 g / comphorsulfonic acid / CH₂Cl₂ / 72 h / 0 - 20 °C

2.1: 59 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

With hydrogenchloride; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1016/j.tet.2003.07.012

Reference yield:

: 2946-01-2
(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

: 685142-66-9
(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaIO₄ / tetrahydrofuran; H₂O

2.1: NaH₂PO₄; H₂O₂; sodium chlorite / acetonitrile; H₂O / 20 °C

2.2: diethyl ether

2.3: DMAP; Et₃N / CH₂Cl₂ / 20 °C

3.1: DBU / CH₂Cl₂ / 5 h / 20 °C

3.2: 29.4 g / H₂ / Pd/C / ethanol / 1 h / 2068.65 Torr

4.1: HCl / 1 h / Heating

4.2: 3.88 g / comphorsulfonic acid / CH₂Cl₂ / 72 h / 0 - 20 °C

5.1: 59 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

With hydrogenchloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; n-butyllithium; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2003.07.012