Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester
• CAS No.: 181960-85-0
• Molecular Formula: C₄₉H₅₆N₂O₁₄S
• Molecular Weight: 929.055

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-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:

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester (181960-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / hydrogen / Pd(OH)2-on-charcoal / tetrahydrofuran; ethanol; H₂O / 3 h / 24 °C

2: 217 mg / tetrahydrofuran / 48 h / 25 °C

With hydrogen; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; water;

DOI:10.1016/0008-6215(96)00090-0

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester (181960-85-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / NaN₃ / acetonitrile / 12 h / Heating

2: 69 percent / hydrogen / Pd(OH)2-on-charcoal / tetrahydrofuran; ethanol; H₂O / 3 h / 24 °C

3: 217 mg / tetrahydrofuran / 48 h / 25 °C

With sodium azide; hydrogen; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1016/0008-6215(96)00090-0

Reference yield:

β-D-glucose pentaacetate (604-69-3) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thioureido]-tetrahydro-pyran-3-yl ester (181960-85-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Me₃SiN₃, SnCl₄ / CH₂Cl₂ / 0.5 h / 24 °C

2: 69 percent / hydrogen / Pd(OH)2-on-charcoal / tetrahydrofuran; ethanol; H₂O / 3 h / 24 °C

3: 217 mg / tetrahydrofuran / 48 h / 25 °C

With trimethylsilylazide; hydrogen; tin(IV) chloride; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1016/0008-6215(96)00090-0

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine

2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranosyl isothiocyanate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

Downstream raw materials:

1-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thiourea

(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

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