(2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one

Base Information

• Chemical Name: (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one
• CAS No.: 99166-46-8
• Molecular Formula: C₃₁H₃₄O₁₀
• Molecular Weight: 566.605

Synonyms:(2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one

Chemical Property of (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one

There total 15 articles about (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one 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: 79.0%

1-methoxy-3-((tert-butyldimethylsilyl)oxy)-4-(benzoyloxy)-1,3-butadiene (87461-94-7) + 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6) → (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one (99166-46-8)

Guidance literature:

magnesium bromide; In benzene; for 6h; Ambient temperature;

DOI:10.1021/ja00291a027

Reference yield: 75.0%

1-benzoyloxy-2-tert-butyldimethylsilyloxy-4-methoxybuta-1,3-diene (91861-07-3) + 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6) → (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one (99166-46-8)

Guidance literature:

With magnesium bromide; In dichloromethane; toluene; at 0 ℃;

DOI:10.1021/ja00311a090

Reference yield: 47.0%

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6) + Benzoic acid (1Z,3E)-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-buta-1,3-dienyl ester (143362-43-0) → (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one (99166-46-8)

Guidance literature:

magnesium bromide; In tetrahydrofuran; for 120h; Ambient temperature;

DOI:10.1021/ja00291a027

upstream raw materials:

1-benzoyloxy-2-tert-butyldimethylsilyloxy-4-methoxybuta-1,3-diene

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose

1-methoxy-3-((tert-butyldimethylsilyl)oxy)-4-(benzoyloxy)-1,3-butadiene

Benzoic acid (1Z,3E)-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-buta-1,3-dienyl ester

Downstream raw materials:

Benzoic acid (2R,3S,4R)-2-[(R)-benzyloxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-methyl]-4-hydroxy-3,4-dihydro-2H-pyran-3-yl ester

6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose

(3S,4S,5S,6S)-6-[(R)-Benzyloxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol

methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-4-(methylsulfonyl)-D-glycero-D-galacto-α-D-galacto-undecapyranoside

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