methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

Base Information

Chemical Name:methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside
CAS No.:527681-52-3
Molecular Formula:C₃₂H₃₄O₉
Molecular Weight:562.617
Hs Code.:

Synonyms:methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

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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 methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

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Technology Process of methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

There total 5 articles about methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside 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%

: 16896-03-0,16896-04-1,30589-89-0,53496-31-4,70831-62-8,103476-40-0,128821-26-1
methyl 2,3-di-O-benzyl-α-D-arabinofuranoside

: 527680-88-2
Benzoic acid (1S,2R,4R,5S)-4-(toluene-4-sulfinyl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

: 527681-52-3
methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

Guidance literature:: Benzoic acid (1S,2R,4R,5S)-4-(toluene-4-sulfinyl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; In dichloromethane; at -78 - -40 ℃; for 0.5h;

methyl 2,3-di-O-benzyl-α-D-arabinofuranoside; In dichloromethane; at -40 ℃; for 0.25h;
DOI:10.1021/ja029302m

Reference yield:

: 16896-03-0,16896-04-1,30589-89-0,53496-31-4,70831-62-8,103476-40-0,128821-26-1
methyl 2,3-di-O-benzyl-α-D-arabinofuranoside

: 329360-17-0
p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside

: 527681-52-3
methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

: Benzoic acid (1S,2R,4S,5S)-4-((2R,3R,4S,5S)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-ylmethoxy)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Guidance literature:: With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -40 ℃; Title compound not separated from byproducts;
DOI:10.1021/ja029302m

Reference yield:

: 65-85-0,8013-63-6
benzoic acid

: 527681-52-3
methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / diisopropyl azodicarboxylate; Ph₃P / tetrahydrofuran / 0.75 h / 0 - 20 °C

2: 4 A molecular sieves; N-iodosuccinimide; silver triflate / CH₂Cl₂ / -40 °C

With N-iodo-succinimide; di-isopropyl azodicarboxylate; 4 A molecular sieve; silver trifluoromethanesulfonate; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja029302m