[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

Base Information

Chemical Name:[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol
CAS No.:75858-32-1
Molecular Formula:C₂₃H₂₈O₆
Molecular Weight:400.472
Hs Code.:

Synonyms:[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

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Chemical Property of [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

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Technology Process of [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

There total 23 articles about [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol 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: 75.0%

: 124-41-4
sodium methylate

: 616895-57-9
(E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester

: 75858-32-1
[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

Guidance literature:: sodium methylate; (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester; In methanol; Heating;

With toluene-4-sulfonic acid; In ethyl acetate;
DOI:10.1016/S0040-4020(03)00370-3

Reference yield: 70.0%

: 67-56-1
methanol

: 616895-54-6
((2S,3R,4S,6R)-6-Allyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-methanol

: 75858-32-1
[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

Guidance literature:: ((2S,3R,4S,6R)-6-Allyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-methanol; With ozone; In methanol;

With dimethylsulfide;

methanol; With bromine; In water;
DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

: 61243-05-8
(S)-1-(α-furyl)-1,2-ethanediol

: 75858-32-1
[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: O₂; TPP / methanol; CH₂Cl₂

1.2: 93 percent / Me₂S

2.1: 66 percent / TsOH; MgSO₄ / acetonitrile

3.1: H₂ / Pd/C / ethyl acetate

3.2: NaHMDS / tetrahydrofuran / -78 °C

3.3: 84 percent / tetrahydrofuran

4.1: 60 percent / Bu₃SnH; LiCl / (Ph₃P)4Pd / diethyl ether

5.1: MCPBA; NaHCO₃ / CH₂Cl₂

5.2: KOH / H₂O

6.1: NaH / dimethylsulfoxide; tetrahydrofuran

7.1: TiCl₄ / CH₂Cl₂ / -78 °C

8.1: O₃ / methanol

8.2: Me₂S

8.3: 70 percent / Br₂ / H₂O

With hydrogen; oxygen; tri-n-butyl-tin hydride; thiamine diphosphate; titanium tetrachloride; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; ozone; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(03)00370-3