(10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

Base Information

Chemical Name:(10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside
CAS No.:122622-25-7
Molecular Formula:C₂₆H₄₂O₆Si
Molecular Weight:478.701
Hs Code.:

(10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

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Chemical Property of (10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

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Technology Process of (10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

There total 23 articles about (10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside 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:

: 122672-66-6
methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

: 122622-25-7
(10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

2: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

3: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

4: dimethylformamide / 2 h / 100 °C

5: NaOMe / methanol / Ambient temperature

6: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

7: tetrahydrofuran / 0.17 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; Celite; sodium methylate; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00283a034

Reference yield:

: 122622-39-3
(2R,4aR,6S,7R,8S,8aR)-7-(2-Hydroxy-ethyl)-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 122622-25-7
(10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

2: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

3: dimethylformamide / 2 h / 100 °C

4: NaOMe / methanol / Ambient temperature

5: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

6: tetrahydrofuran / 0.17 h

With pyridine; 1H-imidazole; thionyl chloride; Celite; sodium methylate; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00283a034

Reference yield:

: 122672-65-5
methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

: 122622-25-7
(10S)-methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((Z)-2-hydroxypropylidene)-2-C-methyl-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 65 percent / KH / tetrahydrofuran / 3 h / 0 °C

2: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

3: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

4: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

5: dimethylformamide / 2 h / 100 °C

6: NaOMe / methanol / Ambient temperature

7: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

8: tetrahydrofuran / 0.17 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; Celite; sodium methylate; sodium acetate; potassium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00283a034