(1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol

Base Information

• Chemical Name: (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol
• CAS No.: 115117-20-9
• Molecular Formula: C₅₁H₅₈O₁₀
• Molecular Weight: 831.016
• Mol file: 115117-20-9.mol

Synonyms:(1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol

Chemical Property of (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol

There total 8 articles about (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol 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:

Toluene-4-sulfonic acid (2S,3S,4S)-4-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-butyl ester → (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol (115117-20-9)

Guidance literature:

With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo00054a006

Reference yield:

2-bromo-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene (92413-82-6,92470-97-8,115224-34-5,115224-37-8) → (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol (115117-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) t-BuLi, 2.) I₂ / 1.) THF, -78 deg C, 2.) THF, -78 deg C

2: 1.) NiCl₂, CrCl₂, 2.) (EtO₂CN=)2, PPh₃, PhCO₂H, 3.) K₂CO₃

3: MCPBA / CH₂Cl₂ / Ambient temperature

With chromium dichloride; iodine; tert.-butyl lithium; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; benzoic acid; nickel dichloride; diethylazodicarboxylate; In dichloromethane;

DOI:10.1021/jo00249a056

Reference yield:

(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal (106929-09-3) → (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol (115117-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) MCPBA, phosphate buffer, 2.) LiAlH₄, 3.) (COCl)2, DMSO

2: 1.) NiCl₂, CrCl₂, 2.) (EtO₂CN=)2, PPh₃, PhCO₂H, 3.) K₂CO₃

3: MCPBA / CH₂Cl₂ / Ambient temperature

With chromium dichloride; lithium aluminium tetrahydride; phosphate buffer; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; benzoic acid; nickel dichloride; diethylazodicarboxylate; In dichloromethane;

DOI:10.1021/jo00249a056

upstream raw materials:

(1S,2R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-en-2-ol

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

2-bromo-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene

(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal

Downstream raw materials:

(2R,3S,4S,5R)-4-Benzyloxy-2,5-bis-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-furan-3-ol