methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate

Base Information

• Chemical Name: methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate
• CAS No.: 438547-23-0
• Molecular Formula: C₂₉H₃₇NO₈Si
• Molecular Weight: 555.7
• Mol file: 438547-23-0.mol

Synonyms:methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate

Chemical Property of methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate

There total 5 articles about methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate 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: 83.0%

3-Benzyloxy-5-nitro-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester (438547-22-9) + 5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-yne (319924-30-6) → methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate (438547-23-0)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 65 ℃; for 2h;

DOI:10.1021/jo049862z

Reference yield:

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (73346-74-4) → methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate (438547-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 2 h / 20 °C

1.2: 76 percent / tetrahydrofuran / 1.5 h / 0 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: 31.6 g / K₂CO₃ / methanol / 0 - 20 °C

4.1: 83 percent / Ph₃P; Pd(OAc)2; Et₃N / tetrahydrofuran / 2 h / 65 °C

With palladium diacetate; oxalyl dichloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation;

DOI:10.1021/jo049862z

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl 3-benzyloxy-4-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethynyl-5-nitrobenzoate (438547-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 2 h / 20 °C

1.2: 76 percent / tetrahydrofuran / 1.5 h / 0 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: 31.6 g / K₂CO₃ / methanol / 0 - 20 °C

4.1: 83 percent / Ph₃P; Pd(OAc)2; Et₃N / tetrahydrofuran / 2 h / 65 °C

With palladium diacetate; oxalyl dichloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation;

DOI:10.1021/jo049862z

upstream raw materials:

3-Benzyloxy-5-nitro-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester

5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-yne

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

tert-butyldimethylsilyl chloride

Downstream raw materials:

methyl 3-benzyloxy-4-[2-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-ethyl]-5-nitrobenzoate