2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid

Base Information

• Chemical Name: 2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid
• CAS No.: 207107-96-8
• Molecular Formula: C₃₈H₄₀O₉
• Molecular Weight: 640.73

Synonyms:2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid

Chemical Property of 2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid

Chemical Property:

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Technology Process of 2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid

There total 2 articles about 2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic 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:

2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid diethyl ester → 2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid (207107-96-8)

Guidance literature:

With sodium hydroxide; In methanol; at 80 ℃; for 3h; Yield given;

DOI:10.1016/S0040-4039(98)00342-6

Reference yield:

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran (3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9) → 2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid (207107-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / TMSOTf / acetonitrile / 18 h / Ambient temperature

2: NaOH / methanol / 3 h / 80 °C

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; In methanol; acetonitrile;

DOI:10.1016/S0040-4039(98)00342-6

Reference yield: 91.0%

2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid (207107-96-8) → 2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propionic acid

Guidance literature:

copper(I) oxide; In acetonitrile; at 80 ℃; for 2h;

DOI:10.1016/S0040-4039(98)00342-6

upstream raw materials:

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

Downstream raw materials:

[(S)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester

[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester

N-[(S)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

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