Reaction:JCGG-RAC0002416

JCGG ID

JCGG-RAC0002416

Submitter

The Noguchi Institute

Reaction ID

R-0000-002416

Regist Date

2012/06/21 19:12:21

REACTANT

MOLECULE ID

JCGG-COM0003141 (Reaction Tree)

Reactant Type

thiomannopyranoside

Mol

0.3 mmol

MOLECULE ID

JCGG-COM0003118 (Reaction Tree)

Skeleton

JCGG-STR031571

Reactant Type

xylopyranoside

Mol

0.33 mmol

MOLECULE ID

JCGG-COM0002535

Reactant Type

BSP

Mol

0.36 mmol

MOLECULE ID

JCGG-COM0002536

Reactant Type

TTBP

Mol

0.45 mmol

MOLECULE ID

JCGG-COM0000761

Reactant Type

Tf2O

Mol

0.36 mmol

PRODUCT

MOLECULE ID

JCGG-COM0003143 (Reaction Tree)

Yield

84%

REACTION DETAIL

Reaction Time

30 minutes, 2.5 hours

Reaction Temp

-65 to -60 degree C, -60 degree C

Solvent

distilled CH2Cl2, distilled CH2Cl2

Comment

1) +all except xylopyranoside, 2) +xylopyranoside

Before the reaction, thiomannopyranoside, BSP, TTBP, and MS 4A were mixed and stirred for 30 minutes at room temperature and then for 5 minutes at -65 degree in Celsius.

MS 4A was included in the solvent.

Both Tf2O and xylopyranoside were added dropwise.

COMMENT

Keywords: xylomannan, antifreeze, Alaskan beetle, Upis ceramboides

There are multiple phases in this reaction.

ATTENTION: There are typos in the written method. (for compound 25 and 26, protocols and xylopyranosides are assigned inversely)

REFERENCE

Reference Id

REF-0000-000339

Issn

Electronic

Doi

10.1021/jo201780e

PubMed ID

21955117

Journal Name

The Journal of organic chemistry. (2011) 76 (21): 8611-20.

Article Title

Synthesis and structural verification of the xylomannan antifreeze substance from the freeze-tolerant Alaskan beetle Upis ceramboides.

Author

David, Crich; Md Yeajur, Rahaman

Affiliation

Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States. dcrich@chem.wayne.edu

Reference Id

REF-0000-000340

Source

J. Org. Chem. 2011, 76, 8611-8620

Doi

10.1021/jo201780e