methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate

Base Information

• Chemical Name: methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate
• CAS No.: 220280-89-7
• Molecular Formula: C₂₇H₃₈O₇SSi
• Molecular Weight: 534.746

Synonyms:methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate

Chemical Property of methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate

Chemical Property:

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Technology Process of methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate

There total 4 articles about methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate 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: 92.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl S-β-D-galactopyranosylmercaptobutyrate (220280-91-1) → methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate (220280-89-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

Reference yield:

methyl 4-mercaptobutanoate (39257-91-5) → methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate (220280-89-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / BF₃*Et₂O / CH₂Cl₂

2: NaOMe / methanol

3: 74 percent / imidazole / dimethylformamide

With 1H-imidazole; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Deacetylation / 3: silylation;

DOI:10.1016/S0040-4039(99)01690-1

Reference yield:

D-galactose pentaacetate (25878-60-8) → methyl 4-S-(6-O'-tert-butyldiphenylsilyl-beta-D-galactopyranosyl)mercaptobutyrate (220280-89-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / BF₃*Et₂O / CH₂Cl₂

2: NaOMe / methanol

3: 74 percent / imidazole / dimethylformamide

With 1H-imidazole; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Deacetylation / 3: silylation;

DOI:10.1016/S0040-4039(99)01690-1

upstream raw materials:

tert-butylchlorodiphenylsilane

methyl S-β-D-galactopyranosylmercaptobutyrate

methyl 4-mercaptobutanoate

D-galactose pentaacetate

Downstream raw materials:

4-[(3aS,4R,6S,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylsulfanyl]-butyric acid methyl ester

methyl 4-S-(3-O'-allyl-2-O'-acetyl-6-O'-tert-butyldiphenylsilyl-β-D-galactopyranosyl)mercaptobutyrate

methyl 4-S-(2-O'-acetyl-6-O'-tert-butyldiphenylsilyl-3,4-O'-isopropylidene-β-D-galactopyranosyl)mercaptobutyrate

methyl 4-S-(2-O'-acetyl-6-O'-tert-butyidiphenyisilyl-β-D-galacto-pyranosyl)mercaptobutyrate

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