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Short Note
Peer-Review Record

N,N-Bis(hexyl α-d-acetylmannosyl) Acrylamide

by Atsushi Miyagawa *, Shinya Ohno and Hatsuo Yamamura
Reviewer 1: Anonymous
Submission received: 7 June 2021 / Revised: 26 June 2021 / Accepted: 20 July 2021 / Published: 22 July 2021
(This article belongs to the Collection Molecules from Side Reactions)

Round 1

Reviewer 1 Report

In this manuscript, the authors described the acryloylation of 6-aminohexyl α-mannoside and the synthesis of N,N-bis(hexyl α-D-acetylmannosyl) acrylamide monomer, which contains two hexyl mannose units and one acrylamide group. Before further evaluate to be published, some points should be addressed.

  1. The authors mentioned 6-Aminohexyl α-D-mannoside (1) was prepared from D-mannose in five steps, the details of synthetic routes and yields should be added in the main text.
  2. The isolated yield of compounds 2 and 3 are very low, the authors mentioned the mixture of 2 and 3 was also obtained, is there any method to separate the mixture in order to improve the isolated yields, or determine the ratio of 2 and 3?
  3. In the synthetic procedure of compound 1, the authors used acetylation to protect the –OH and deacetylation to release the –OH, for the synthesis of 2 and 3, compound 1 repeated acetylation after treated with with acryloyl chloride, did the authors try direct acryloylation after glycosylation with 6-aminohexan-1-ol?
  4. The authors used NMR spectrum and MS to confirm the structure of compound 3, but the transformation of 1 to 3 seems abnormal, more structure characterization should be performed to verify the structure of 3.
  5. The MS data of compound 3, m/z: [M+Na]+ Calcd for C43H65N1Na1O21+: 954.3941, found: 954.2400; [M+K]+ Calcd for C43H65K1N1O21+: 123 970.3681, found: 970.2095. The error value should be less than 5 ppm.
  6. In abstract, line 12, “unexpexted” should be “unexpected”

Author Response

Please see the attachment.

Author Response File: Author Response.docx

Round 2

Reviewer 1 Report

This manuscript was improved according to the reviewer's comments, I suggest some points still needs to be addressed:

  1. The origin of compound 3 is better to be clarified. Did the authors try to obtain compound 3 from compound 2 with compound 1?
  2. The IR spectrum of compound 3 should be provided.

Author Response

Please see the attachment.

Author Response File: Author Response.pdf

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