(R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide

Base Information

• Chemical Name: (R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide
• CAS No.: 1065473-26-8
• Molecular Formula: C₃₉H₄₅NO₆S
• Molecular Weight: 655.855

Synonyms:(R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide

Chemical Property of (R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide

Chemical Property:

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Technology Process of (R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide

There total 1 articles about (R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide 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: 70.0%

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose (113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9) + (R)-2-methylpropane-2-sulfinamide (196929-78-9) → (RS)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide (1065473-26-8)

Guidance literature:

With copper(II) sulfate; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol048750r

Reference yield: 71.0%

methylmagnesium bromide (75-16-1) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (RS)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide (1065473-26-8) → [(R)-1-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (767344-26-3)

Guidance literature:

methylmagnesium bromide; (R_S)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide; In dichloromethane; at -78 ℃; for 1.33333h;

With hydrogenchloride; methanol; In 1,4-dioxane;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; Further stages.;

DOI:10.1039/b705750d

Reference yield:

benzylmagnesium chloride (6921-34-2) + (RS)-2-methylpropane-2-sulfinic acid [1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)methylidene]amide (1065473-26-8) → 2-Methyl-propane-2-sulfinic acid [(R)-2-phenyl-1-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amide

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; at -78 ℃;

DOI:10.1021/ol048750r

upstream raw materials:

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

(R)-2-methylpropane-2-sulfinamide

Downstream raw materials:

[(R)-1-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

[(R)-Phenyl-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-carbamic acid tert-butyl ester

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