((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Base Information

Chemical Name:((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester
CAS No.:381724-74-9
Molecular Formula:C₄₀H₄₆O₈
Molecular Weight:654.8
Hs Code.:

Synonyms:((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

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Chemical Property of ((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

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Technology Process of ((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

There total 1 articles about ((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic 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: 84.0%

: 150942-98-6
t-butyl lithioacetate

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 381724-74-9
((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Guidance literature:: In tetrahydrofuran; at -78 - 20 ℃; for 1h;
DOI:10.1055/s-2001-16797

Reference yield: 100.0%

: 381724-74-9
((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

: 381724-75-0
((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1055/s-2001-16797

Reference yield:

: 381724-74-9
((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

: (S)-4-[2-((2S,3R,4S,5R,6R)-2-Benzoylamino-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-2-tert-butoxycarbonylamino-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 °C

2.1: TMSOTf / CH₂Cl₂ / 2 h / 0 °C

2.2: 75 percent / DIEA / CH₂Cl₂ / 12 h / 0 - 20 °C

3.1: H₂ / Pd(OH)2 / methanol

With trimethylsilyl trifluoromethanesulfonate; hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; 2.1: Ritter reaction;
DOI:10.1055/s-2004-837204