{(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol

Base Information

• Chemical Name: {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol
• CAS No.: 96961-24-9
• Molecular Formula: C₆₁H₇₂N₂O₁₄
• Molecular Weight: 1057.25

Synonyms:{(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol

Chemical Property of {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol

Chemical Property:

Purity/Quality:

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Technology Process of {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol

There total 11 articles about {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol 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: 92.0%

[(2R,3S,4R,5R,6S)-5-Azido-6-((2R,3S,4R,5R,6R)-5-azido-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-3-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol → {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol (96961-24-9)

Guidance literature:

With hydrogen sulfide; In pyridine; water; at 20 ℃; for 19h;

DOI:10.1016/0008-6215(85)85173-9

Reference yield:

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl bromide (70056-63-2) → {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol (96961-24-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / silver zeolite / CH₂Cl₂

2: 100 percent / trifluoroacetic acid / 4 h / 20 °C

3: 85 percent / NH₂NH_2.HOAc / dimethylformamide / 1 h / 20 °C

4: 100 percent / oxalyl bromide / CHCl₃; dimethylformamide

5: 20 percent / silver zeolite / CH₂Cl₂ / 48 h / 20 °C / molecular sieves 4 Angstroem

6: 100 percent / Zemplen deacetylation

7: 92 percent / H₂S / pyridine; H₂O / 19 h / 20 °C

With Oxalyl bromide; silver zeolite; hydrogen sulfide; hydrazinium monoacetate; In pyridine; dichloromethane; chloroform; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/0008-6215(85)85173-9

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) → {(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol (96961-24-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / silver zeolite / CH₂Cl₂

2: 100 percent / trifluoroacetic acid / 4 h / 20 °C

3: 85 percent / NH₂NH_2.HOAc / dimethylformamide / 1 h / 20 °C

4: 100 percent / oxalyl bromide / CHCl₃; dimethylformamide

5: 20 percent / silver zeolite / CH₂Cl₂ / 48 h / 20 °C / molecular sieves 4 Angstroem

6: 100 percent / Zemplen deacetylation

7: 92 percent / H₂S / pyridine; H₂O / 19 h / 20 °C

With Oxalyl bromide; silver zeolite; hydrogen sulfide; hydrazinium monoacetate; In pyridine; dichloromethane; chloroform; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/0008-6215(85)85173-9

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl bromide

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

4-O-(6-O-Acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-desoxy-β-D-glucopyranose

1,6-Di-O-acetyl-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-2-azido-3-O-benzyl-2-desoxy-α-D-glucopyranose

Downstream raw materials:

C₈₉H₁₂₄N₂O₁₈

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