(2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol

Base Information

• Chemical Name: (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol
• CAS No.: 110046-08-7
• Molecular Formula: C₂₆H₃₆O₈
• Molecular Weight: 476.567

Synonyms:

Chemical Property of (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol

There total 9 articles about (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol 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:

Benzoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((1R,2R,3S)-2,3,4-trihydroxy-1,3-dimethyl-butyl)-tetrahydro-pyran-3-yl ester (110046-07-6) → (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol (110046-08-7)

Guidance literature:

With sodium methylate; In methanol; for 0.0666667h; Ambient temperature;

DOI:10.1021/jo00229a015

Reference yield:

methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside (110045-79-9) → (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol (110046-08-7)

Guidance literature:

Multi-step reaction with 9 steps

1: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: 2,3-dichloro,5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; dioxane; H₂O / 4 h / Ambient temperature

3: pyridinium chlorochromate, Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

4: 94 percent / tetrahydrofuran / 1 h / Ambient temperature

5: pyridine / 16 h / 40 °C

6: thionyl chloride / pyridine / 0.08 h / 0 °C

7: dl-camphorsulfonic acid / methanol / 20 h / Ambient temperature

8: 85 percent / N-methylmorpholine N-oxide, osmium tetraoxide / 2-methyl-propan-2-ol; H₂O; acetone / 2 h / Ambient temperature

9: sodium methoxide / methanol / 0.07 h / Ambient temperature

With pyridine; dmap; florisil; osmium(VIII) oxide; thionyl chloride; Celite; camphor-10-sulfonic acid; sodium methylate; sodium acetate; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo00229a015

Reference yield:

(2R,3R,4S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(isopropyl-dimethyl-silanyloxy)-6-methoxy-4-methyl-octahydro-pyrano[3,2-b]pyran-2-ol → (2S,3R,4R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methyl-pentane-1,2,3-triol (110046-08-7)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridinium chlorochromate, Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

2: 94 percent / tetrahydrofuran / 1 h / Ambient temperature

3: pyridine / 16 h / 40 °C

4: thionyl chloride / pyridine / 0.08 h / 0 °C

5: dl-camphorsulfonic acid / methanol / 20 h / Ambient temperature

6: 85 percent / N-methylmorpholine N-oxide, osmium tetraoxide / 2-methyl-propan-2-ol; H₂O; acetone / 2 h / Ambient temperature

7: sodium methoxide / methanol / 0.07 h / Ambient temperature

With pyridine; florisil; osmium(VIII) oxide; thionyl chloride; Celite; camphor-10-sulfonic acid; sodium methylate; sodium acetate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo00229a015

upstream raw materials:

Benzoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((1R,2R,3S)-2,3,4-trihydroxy-1,3-dimethyl-butyl)-tetrahydro-pyran-3-yl ester

methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1,3-dimethyl-butyl]-6-methoxy-tetrahydro-pyran-3-ol

methyl 2,3-di-O-benzyl-6-deoxy-6-C-methyl-7-O-(tert-butyldimethylsilyl)-L-threo-α-D-gluco-octopyranosiduronic acid γ-lactone

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