(S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Base Information

• Chemical Name: (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester
• CAS No.: 863890-86-2
• Molecular Formula: C₇₆H₈₀N₄O₁₄
• Molecular Weight: 1273.49

Synonyms:(S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Chemical Property of (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

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Technology Process of (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

There total 5 articles about (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester 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: 60.0%

C54H56FN3O9 + N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester (110797-35-8) → (S)-3-[(2R,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester + (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester (863890-86-2)

Guidance literature:

With zirconocene dichloride; 4 A molecular sieve; silver perchlorate; In dichloromethane; at -78 - 20 ℃; for 8h;

DOI:10.1021/ol0514193

Reference yield:

C54H56FN3O9 (863891-02-5) + N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester (110797-35-8) → (S)-3-[(2R,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester + (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester (863890-86-2)

Guidance literature:

With zirconocene dichloride; 4 A molecular sieve; silver perchlorate; In dichloromethane; at -78 - 20 ℃; for 8h;

DOI:10.1021/ol0514193

Reference yield:

2,2,2-Trichloro-acetimidic acid (3R,4R,5R,6R)-3-azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester + N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester (110797-35-8) → (S)-3-[(2R,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester + (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester (863890-86-2)

Guidance literature:

With zirconocene dichloride; 4 A molecular sieve; silver perchlorate; In dichloromethane; at -78 - 20 ℃; for 8h;

DOI:10.1021/ol0514193

upstream raw materials:

N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester

C₅₄H₅₆FN₃O₉

2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride

benzyl bromide

Downstream raw materials:

(S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

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