(2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid
• CAS No.: 727380-42-9
• Molecular Formula: C₅₁H₅₅N₃O₁₂
• Molecular Weight: 902.011

Synonyms:

Chemical Property of (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

There total 3 articles about (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid 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:

(2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde → (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid (727380-42-9)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at -10 - 20 ℃;

DOI:10.1002/ejoc.200300791

Reference yield:

allyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (628280-88-6) → (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid (727380-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: 1.86 g / NaH₂PO₄; 2-methyl-2-butene; NaO₂Cl / H₂O; 2-methyl-propan-2-ol / -10 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Swern-oxidation;

DOI:10.1002/ejoc.200300791

Reference yield:

allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (628281-08-3) → (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid (727380-42-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / PhBCl₂; Et₃SiH; 4 Angstroem molecular sieves / diethyl ether / -40 °C

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3: 1.86 g / NaH₂PO₄; 2-methyl-2-butene; NaO₂Cl / H₂O; 2-methyl-propan-2-ol / -10 - 20 °C

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; phenylborondichloride; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane; water; tert-butyl alcohol; 2: Swern-oxidation;

DOI:10.1002/ejoc.200300791

upstream raw materials:

allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

allyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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