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

Base Information

• Chemical Name: [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde
• CAS No.: 256397-91-8
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 256397-91-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde 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: 86.0%

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol (75858-32-1) → [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde (256397-91-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield: 67.0%

[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (406684-08-0) → [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde (256397-91-8)

Guidance literature:

[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester; hydrogenchloride; In methanol; at 0 - 20 ℃; for 0.5h;

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;

With triethylamine; In dichloromethane; at -78 ℃; for 7h;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield:

(S)-1-(α-furyl)-1,2-ethanediol (61243-05-8) → [2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde (256397-91-8)

Guidance literature:

Multi-step reaction with 9 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

9.1: 86 percent / Dess-Martin periodinane / CH₂Cl₂

With hydrogen; oxygen; tri-n-butyl-tin hydride; thiamine diphosphate; titanium tetrachloride; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; 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

upstream raw materials:

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

[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

(S)-1-(α-furyl)-1,2-ethanediol

(-)-(1S,5S)-Isolevoglucosenone

Downstream raw materials:

(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

(1S,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-(2,4-dichlorobenzoyloxy)-2-methoxycarbonyl-3-methylhex-4-enoate

(1S,4R)-1-O-allyloxycarbonyl-4-O-tert-butyldimethylsilyl-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]pent-2-yne-1,4-diol