ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside
CAS No.:260779-96-2
Molecular Formula:C₃₆H₄₄O₈S
Molecular Weight:636.807
Hs Code.:

Synonyms:ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

There total 1 articles about ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-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: 64.0%

: 40052-13-9
mono-tert-butyl malonate

: 39483-51-7,119645-03-3,126461-54-9,128850-50-0
ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 260779-96-2
ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1002/(SICI)1099-0690(200001)2000:1<181::AID-EJOC181>3.0.CO;2-7

Reference yield: 100.0%

: 260779-96-2
ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

: 260779-97-3
ethyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1002/(SICI)1099-0690(200001)2000:1<181::AID-EJOC181>3.0.CO;2-7

Reference yield:

: 260779-96-2
ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

: (2S,3R,4R,5S,6R)-2-Benzyloxy-6-benzyloxymethyl-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / TFA / 3 h / 20 °C

2: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 78 percent / HCl/Et₂O; NaCNBH₃ / tetrahydrofuran

4: 17 percent / 4A molecular sieves; NIS; TMSOTf / CH₂Cl₂ / 0.17 h / -30 °C

5: NaOMe / methanol / 3 h / 20 °C

With hydrogenchloride; dmap; N-iodo-succinimide; diethyl ether; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium cyanoborohydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrolysis / 2: Acylation / 3: Ring cleavage / 4: Cyclization / 5: deacylation;
DOI:10.1016/S0040-4020(99)01053-4