methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside
• CAS No.: 557088-28-5
• Molecular Formula: C₃₀H₃₄O₆
• Molecular Weight: 490.596

Synonyms:methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside

Chemical Property of methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside

There total 6 articles about methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside 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: 65.0%

methyl 4-allyl-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside → methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside (365418-30-0) + methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside (557088-28-5)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; at 20 ℃; for 6h;

DOI:10.1021/ja010641+

Reference yield:

methyl 2,3,6-tri-O-acetyl-4-allyl-4-deoxy-α-D-glucopyranoside → methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside (557088-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOMe / methanol; tetrahydrofuran

1.2: 75 percent / NaH / dimethylformamide / 12 h / 23 °C

2.1: 203 mg / OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium methylate; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo030039x

Reference yield:

(2S,3R,4S,6S)-5-Allyl-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4-diol → methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside (557088-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide; various solvent(s) / 12 h / 60 °C

2: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ja010641+

upstream raw materials:

benzyl bromide

methyl 2,3,6-tri-O-acetyl-4-deoxy-4-iodo-α-D-galactopyranoside

methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside

Downstream raw materials:

((2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid

((2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-[2-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-allyl]-2-methoxy-tetrahydro-pyran

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