(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

Base Information

• Chemical Name: (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
• CAS No.: 115094-69-4
• Molecular Formula: C₅₁H₅₈O₉
• Molecular Weight: 815.016
• Mol file: 115094-69-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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:

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,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 (115094-69-4)

Guidance literature:

Multi-step reaction with 2 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

With chromium dichloride; iodine; tert.-butyl lithium; potassium carbonate; triphenylphosphine; benzoic acid; nickel dichloride; diethylazodicarboxylate;

DOI:10.1021/jo00249a056

Reference yield:

(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal (106929-09-3) → (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 (115094-69-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/jo00249a056

Reference yield:

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (103795-12-6) + (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-iodo-allyl)-tetrahydro-pyran → (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 (115094-69-4)

Guidance literature:

With chromium dichloride; potassium carbonate; triphenylphosphine; benzoic acid; nickel dichloride; diethylazodicarboxylate; Multistep reaction;

DOI:10.1021/jo00249a056

upstream raw materials:

(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

(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

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