ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside
• CAS No.: 195192-33-7
• Molecular Formula: C₃₀H₃₄O₅S
• Molecular Weight: 506.663

Synonyms:ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

Chemical Property of ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

There total 4 articles about ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside 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: 70.0%

ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside (128850-48-6) + 2,2-dimethoxy-propane (77-76-9) → ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside (195192-33-7)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; for 16h;

Reference yield:

ethyl 1-thio-α-D-mannopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside (195192-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; 4-dimethylaminopyridine

2: p-toluenesulfonic acid / dimethylformamide / 2 h / 20 °C

With pyridine; dmap; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: Alkylation / 2: acetalization;

DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

trityl chloride (76-83-5) → ethyl 2,3-O-isopropylidene-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside (195192-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; 4-dimethylaminopyridine

2: p-toluenesulfonic acid / dimethylformamide / 2 h / 20 °C

With pyridine; dmap; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: Alkylation / 2: acetalization;

DOI:10.1016/S0957-4166(99)00554-6

upstream raw materials:

ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

2,2-dimethoxy-propane

ethyl 1-thio-α-D-mannopyranoside

trityl chloride

Downstream raw materials:

ethyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-6-O-trityl-α-D-mannopyranoside

ethyl 2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

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