(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 98931-42-1
• Molecular Formula: C₄₂H₅₂N₂O₁₂
• Molecular Weight: 776.881

Synonyms:

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

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MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 1 articles about (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl 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: 84.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (98931-42-1,98976-14-8,130015-85-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; 1) 0 deg C, 2) RT;

DOI:10.1271/bbb1961.54.1401

Reference yield: 93.0%

(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (98931-42-1,98976-14-8,130015-85-9) → (S)-2-Amino-3-phenyl-propionic acid (2S,3R,4S,5R,6R)-3-((S)-2-amino-3-phenyl-propionyloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yl ester; hydrochloride (130015-88-2)

Guidance literature:

With hydrogenchloride; formic acid; In ethyl acetate; Ambient temperature;

DOI:10.1271/bbb1961.54.1401

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (4aR,6S,7R,8S,8aR)-7-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (98931-42-1,98976-14-8,130015-85-9) → methyl 2,3-di-O--α-D-glucopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4N HCl, formic acid / ethyl acetate / Ambient temperature

2: 82 percent / 1-hydroxybenzotriazole, DCC / dimethylformamide / 1) 0 deg C, 2) RT

With hydrogenchloride; formic acid; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1271/bbb1961.54.1401

upstream raw materials:

methyl 4,6-O-benzylidene-α-D-glucopyranoside

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(S)-2-Amino-3-phenyl-propionic acid (2S,3R,4S,5R,6R)-3-((S)-2-amino-3-phenyl-propionyloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yl ester; hydrochloride

C₅₁H₆₂N₈O₁₄*2ClH

methyl 2,3-di-O-(L-phenylalanyl-L-phenylalanyl-L-phenylalanyl)-α-D-glucopyranoside

C₅₃H₆₆N₄O₁₄

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