(2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 104845-97-8
• Molecular Formula: C₄₇H₅₅NO₁₄
• Molecular Weight: 857.952

Synonyms:

Chemical Property of (2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 1 articles about (2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl 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: 80.0%

2-Methoxypropene (116-11-0) + (2R,4R,5R,6R)-6-((S)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104845-95-6,106455-74-7) → (2S,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester + (2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104845-96-7,104845-97-8)

Guidance literature:

DOI:10.1016/S0040-4039(00)84197-0

Reference yield: 44.0%

methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)onate (148152-74-3) + (2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104845-96-7,104845-97-8) → C64H77NO25 (104845-98-9,104845-99-0) + C64H77NO25 (104845-98-9,104845-99-0)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In nitromethane;

DOI:10.1016/S0040-4039(00)84197-0

Reference yield:

(2R,4R,5R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104845-96-7,104845-97-8) → C51H61NO21 (104846-13-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 44 percent / HgBr₂,Hg(CN)2 / nitromethane

2: CF₃CO₂H

3: 1)NaOMe, 2)NaOH, H₂O, MeOH

With methanol; sodium hydroxide; water; sodium methylate; mercury(II) cyanide; trifluoroacetic acid; mercury dibromide; In nitromethane;

DOI:10.1016/S0040-4039(00)84197-0

upstream raw materials:

2-Methoxypropene

(2R,4R,5R,6R)-6-((S)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-2-((2R,3S,4R,5R,6S)-3,4,6-tris-benzyloxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

C₆₄H₇₇NO₂₅

C₆₄H₇₇NO₂₅

C₅₁H₆₁NO₂₁

C₆₁H₇₃NO₂₅

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