(2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde

Base Information

• Chemical Name: (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde
• CAS No.: 229469-34-5
• Molecular Formula: C₃₅H₃₆O₇
• Molecular Weight: 568.667

Synonyms:(2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde

Chemical Property of (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde

There total 10 articles about (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde 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: 90.0%

3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytrityloxymethyl)-1-α-methyl-D-ribofuranose (229469-33-4) → (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde (229469-34-5)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dimethyl sulfoxide; 1.) 10 deg C, 1 h, 2.) room temperature, 6 h;

DOI:10.1016/S0040-4020(99)00394-4

Reference yield:

methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside (164454-52-8) → (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde (229469-34-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) DCC, TFA, pyridine, 2.) oxalic acid / 1.) DMSO, Et₂O, room temperature, 5 h, 2.) MeOH, room temperature, 1 h

2: 91 percent / sodium t-pentoxide / diethyl ether; benzene / 1.) room temperature, 6 h, 2.) -10 deg C, 1 h

3: 88 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

4: pyridine / 15 h / Ambient temperature

5: 76 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

6: 1.) 9-BBN, 2.) sodium perborate tetrahydrate / 1.) room temperature, 1 h; 40 deg C, overnight, 2.) H₂O, EtOH, 50 deg C, 4 h

7: pyridine / Ambient temperature

8: TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

9: 90 percent / DCC, TFA, pyridine / dimethylsulfoxide / 1.) 10 deg C, 1 h, 2.) room temperature, 6 h

With pyridine; sodium perborate; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; oxalic acid; sodium tert-pentoxide; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; diethyl ether; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4020(99)00394-4

Reference yield:

methyl D-arabinofuranoside (56607-40-0) → (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde (229469-34-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h

2: 1.) DCC, TFA, pyridine, 2.) oxalic acid / 1.) DMSO, Et₂O, room temperature, 5 h, 2.) MeOH, room temperature, 1 h

3: 91 percent / sodium t-pentoxide / diethyl ether; benzene / 1.) room temperature, 6 h, 2.) -10 deg C, 1 h

4: 88 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

5: pyridine / 15 h / Ambient temperature

6: 76 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

7: 1.) 9-BBN, 2.) sodium perborate tetrahydrate / 1.) room temperature, 1 h; 40 deg C, overnight, 2.) H₂O, EtOH, 50 deg C, 4 h

8: pyridine / Ambient temperature

9: TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

10: 90 percent / DCC, TFA, pyridine / dimethylsulfoxide / 1.) 10 deg C, 1 h, 2.) room temperature, 6 h

With pyridine; sodium perborate; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; oxalic acid; sodium tert-pentoxide; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; diethyl ether; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4020(99)00394-4

upstream raw materials:

3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytrityloxymethyl)-1-α-methyl-D-ribofuranose

methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside

methyl D-arabinofuranoside

(2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol

Downstream raw materials:

(1R,3R,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-9-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane

(1R,3S,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-9-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane

(1R,3S,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-7-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane

(1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane

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